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AMERICAN CHEMICAL SOCIETY October 5, 1961, Vol. 83, No. 19 Acid-Base Equilibria in Acetonitrile. Spectrophotometric and Conductometric Determination of the Dissociation of Various Acids. I. M . Kolthoff, S . Bruckenstein and M . K . Chantooni, J r . . . . . . . . . . . . . . . The Thermal Decomposition of cis-l,2-Dimethylcyclobutane. H . R. Gerberich and W . D. Walters . . . . . . . . . . . . . . . . . Studies in Non-Stoichiometry. Electrical Conductivity and Carrier Mobility in Lithium Tungsten Bronzes. M . J . Sienko and Thu Ba Nguyen Truong . . . . . . . . . . . . . Nitrite Substitution in Chloroammineplatinum (IV) Complexes. Herbert R. Ellison, Fred Basolo and Ralph G. Pearson . . . . . . . Substituent Effects in the Chronopotentiometric Oxidation of Ferrocenes. George L. K . Hoh, William E . McEwen and Jacob Kleinberg . . . The Kinetics and Mechanism of the Reaction of Borohydrides with Weak Acids. Raymond E . Dessy and Edward Grannen, Jr. . . . . . n-Alkyl Perchlorates: Preparation, Study and Stabilization. Jack Radell, J . W . Connolly and A . J . Raymond. . . . . . . . . . . . Kinetics of the Ethoxide-catalyzed Addition of Aryl Thiols to Ethyl Phenylpropiolates Structure-Reactivity Correlations. G. S. Krishnamurthy and Sidney I. Miller. . . . . . . . . Relative Rates of Grignard Addition and Reduction Reactions. John Miller, George Gregoriou and Harry S . Mosher . . . . . . . . . . . Application of the Favorskii Rearrangement to, 2,3-Epoxycyclohexanones. Herbert 0. House and W . Franklin Gilmore. . . . . . . . . . The Stereochemistry of the FavorskiI Rearrangement. Herbert 0. House and W . Franklin Gilmore . . . . . . . . . . . . . The Absolute Configurations of Some Simple Norbornane Derivatives. A Test of the “Conformational Asymmetry” Model. Jerome A . Berson, Jasjit Singh Walia, Allen Remanick, Shigeto Suzuki, P. Reynolds-Warnhoff and David Willner . . . . . . . . . . . . . . Bicyclo [2.1.1 ]hexane Derivatives. Kenneth B . Wiberg, Betty R. Lowry and Thomas H . Colby Stereochemistry of Hydroanthracenes. Richard K . Hill,James G. Martin and William H . Stouch . . . . . . . . . . . . . . . . . Structure and the Optical Rotatory Dispersion of Saturated Ketones. William Mofitt, R. B . Woodward, A . Moscowitz, W . Klyne and Carl Djerassi . . . . . . . . . . . . . . . . . An Acid-catalyzed Cleavage of Sulfoxides. William J . Kenney, James A . Walsh and Derek A . Davenport. . . . . . . . . . . . . . . The Reaction of Cobalt Hydrotetracarbonyl with Olefins. Richard F . Heck and David S. Breslow. . . . . . . . . . . . . . . . . Mechanisms of Elimination Reactions. XKIII. The Phenyllithium-induced Dehydrochlorination of the Isomeric Chlorodiphenylethenes. Stanley J . Cristol and Robert S . Bly, Jr. . , , . Mechanism of a-Elimination by Hydroxide Ion on p-Nitrobenzylsulfonium Ion in Aqueous Solution. C. Gardner Swain and Edward R. Thornton . . . . . . . . . . . . . . . . ~

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The Reaction of Dichlorocarbene with 2H-1Benzothiopyran and 4H-1-Benzothiopyran. William E. Parham and Robert Koncos . . , , Potential Purine Antagonists. XXVII. Synthesis and Reactions of Some Purinesulfonyl Fluorides. Alden G. Beaman and Roland K . Robins . . . . . . . . . . . . . . . . . The Biosynthesis of Opium Alkaloids. Alkaloid Interconversions in Papaver somniferum and P . orientale. Frank R. Stermitz and Henry Rapoport . . . . . . . . . . . . . . . . Studies on Synthetic Polypeptide Antigens. 111. The Synthesis and Physico-Chemical Properties of a Group of Linear-Chain Antigens. Edward Friedman, Thomas J. Gill III and Paul Doty . . . . . . . . . . . . . . . . Insulin Peptides. I. Synthesis of Cysteine Containing Peptides Related to the A-Chain of Sheep Insulin. Panayotis G. Katsoyannis . Insulin Peptides. 11. Synthesis of a Protected Pentapeptide. Containing the C-Terminal Sequence of the A-Chain of Insulin. PanayotisG. KatsoyannisandKenjiSuzuki . . . . . Nucleosides. XI. Synthesis of 1-p-n-Arabinofuranosyl-5-fluorouracil and Related Nucleosides. Naishun C. Yung, Joseph H . Burchenal, Ronald Fecher, Robert Duschinsky and Jack J. Fox. . . . . . . . . . . . . . . . . Nucleosides. XII. Direct Synthesis of 2’Deoxycytidine and its a-Anomer. Jack J . Fox, Naishun C. Yung, Iris Wempen and Max Hofer. . . . . . . . . . . . . . . . . . . Vinyl Ethers of Carbohydrates. I. Methyl 2-0-Vinyl-WD-glucopyranoside. Archie J . Deutschman, Jr. and Henry W . Kircher . , . Weak Acid-catalyzed Rearrangement of the Dihydroxyacetone Side Chain in Steroids. Hershel L. Herzog, Margaret Jevnik Gentles, Helen Marshall and E . B . Hershberg . . . . . A New Photochemical Reaction. D . H. R . Barton, J . M . Beaton, L. E . Geller and M . M . Pechet . . . . . . . . . . . . . . . . . . A Synthesis of Aldosterone Acetate. D . H . R. Barton and J . M . Beaton . . . . . . . . . Preparation and Characterization of Dodecaphenylcyclohexasilane. H . J . S. Winkler, A. W. P . Jarvie, D . J . Peterson and H . Gilman.

Communications to t h e Editor Biosynthesis in the Amaryllidaceae. Tyrosine and Norbelladine as Precursors of Haemanthamine. A. R. Battersby, H . M . Fales and W . C. Wildman . . . . . . . . . . . . . Salts of the Heptaphenyltropylium Ion and their Stability. Merle A. Battiste . . . . . A Non-Enzymatic Olefinic Hydration Under Neutral Conditions. The Kinetics of the Hydration of Fumaric Acid Monoanion. Myron L.Bender and Kenneth A . Connors . . . Studies on d-Orbital Conjugation. I. The Absence of a Through-Conjugation Effect in Some Sulfone Carbanions. Ronald Breslow and Ern0 Mohacsi . . . . . . . . . . . . Neptunium(V1) in Molten Nitrates. Donald Cohen . . . . . . . . . . . . . . . . . . Catalysis of the Hydration of Acetylenic Compounds by Ruthenium(II1) Chloride. J . Halpern, B . R. James and A . L . W . Kemp . . Reduction of Silver Amine Complexes by Carbon Monoxide. S. Nakamura and J . Halpern . . Reactivity of Cyclic Peptides. I. Transannular Histidine-0-Acetyltyrosine Interaction. Kenneth D. Kopple and Danute E. Nitecki. . . A Methylated Derivative of Tetrahydrofoliate as an Intermediate of Methionine BiosynVOL. 53, NO. 12

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Tables of Contents of ACS PUBLICATIONS thesis. Allan R. Larrabee, Spencer Rosenthal, Renata E . Cathou and John M . Buchanan . . The Use of a Proton-Proton Spin Decoupling Method for the Determination of Nuclear Magnetic Resonance Chemical Shifts. Stanley L . Manatt and Daniel D. Elleman. . . . . . ( &)Trans - 2,3 - dihydro - 3 - hydroxyanthranilic Acid. A New Amino Acid Produced by Streptomyces aureofaciens. J . R. D . McCormick, Jules Reichenthal, Ursula Hirsch and Newel1 0. Sjolander . . . . . . . . . . Electrophilic Reactions of Argentous and Mercuric Fluorides with Fluoroolefins in Hydrogen Fluoride. William T . Miller, Jr., Mark B. Freedman, John H . Fried and Heinz F. Koch. . Mechanism of Thiamine Action: A New Type of “High Energy” Bond. Charles P . Nash, Clifford W . Olsen, Fred G. White and Lloyd L. Ingraham . . . . . . . . . . . . . . . Serratamolide A. Metabolic Product of Serratia. Harry H. Wasserman, Janis J . Keggi and James E . McKeon . . . . . . . . . . . . Oxazahydroborate Ions. Robert A . Wiesboeck, Anthony R. Pitochelli and M . Frederick Hawthorne . . . . . . . . . . . . . . . . . . Molecular Detachment of Hydrogen Chloride in the Photolysis of cis- 1,2-Dichloroethylene. M . H . J. Wijnen. . . . . . . . . . . . .

Book Reviews Cobalt: Its Chemistry, Metallurgy and Uses. ACS Monograph 149. Edited by Roland S. Young. Review by Arthur W .Adamson. . . Properties and Structure of Polymers. By Arthur V. Tobolsky. Review by Turner Alfrey, Jr.. . . . . . . . . . . . . . . . The Biochemistry of Mucopolysaccharides of Connective Tissue. Biochemistry Society Symposium No. 20 held a t the Royal College of Surgeons, London, on 13 February, 1960. Organized by J. K. Grant. Edited by F. Clark and J. K. Grant. Review by Walter F. Goebel . . . . . . . . . . . . . . . . . . Mineral Metabolism. By Advanced Treatise. Vol. I. Principle, Processes, and Systems. Part A. Edited by U. C. Comar and Felix Bronner. Review by Harold C. Hodge . . . Viscoelastic Properties of Polymers. By John D. Ferry. Review by Maurice L. Huggins . . Introduction t o Solids. By Leonid V. Azaroff. Review by Walter J . Moore . . . . . . . . Photoconductivity of Solids. By Richard H. Bube. Review by JohnTurkevich . . . . . Organometallic Chemistry. Edited by W. H. Zeiss. Review by Irving Wender . . . . . . Cahiers de Synthhse Organique. Methodes et Tableaux D’Application. Volume VII. Cyclisations. By Jean Mathieu, Andre Allais, et Jacques Valls. Cahiers de Synthese Organique. Methoces et Tableaux D’Application. Volume VIII. Cyclisations. By Jean Mathieu, Andre Allais, et Jacques Valls. Review by Richard H. W i l e y . . . . . . . . Books Received . . . . . . . . . . . . . . .

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AMERICAN CHEMICAL SOCIETY October 20, 1961, Vol. 83, No. 20 The Kinetics of Three-step Competitive Consecutive Second-order Reactions. 11. W . J . Svirbely and J a y A . Blauer . . . . . . . . 4115 The Kinetics of the Alkaline Hydrolysis of 1,3,5Tricarbomethoxybenzene. W . J . Svirbely and J a y A . Blauer . . . . . . . . . . . . . . 4118 Microwave Absorption and Molecular Structure in Liquids. XLI. The Dielectric Relaxation INDUSTRIAL AND ENGINEERING CHEMISTRY

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of Three Substituted Naphttalenes in a Slightly Viscous and a Very Viscous Solvent. Eugene L. Grubb and Charles P . Smyth . . . . Synthesis of Arylphosphonous Dichlorides by Reduction of Diazonium Fluoroborate-Phosphorus Trichloride Reaction Products. Louis D. Quin and J . Stevenson Humphrey, J r . . . . Electric Moments and Structures of Organosilicon Compounds. IV. TLe Silicon-Hydrogen Bond. A n n a M . Coleman and Henry Freiser . . . . . . . . . . . . . . . . . synthesis of Diborane by the Hydrogenolysis of Trialkylborons: by Ralph Klein, Arthur Bliss, Louis Schoen and Herbert G. Nadeau . . . . Thermal Stability of Substituted Borazoles. H . C . Newsom, W .D. English, A . L. McCloskey and W . G. Woods . . . . . . . . . . . . Molecular Addition Compounds of Boron. V. Proton Chemical Shifts and the Stability of T. D . Coyle and F. G. A . Stone. . . . . . . Stability of the Mixed Complex FeSCNF+. Richard G. Yalman . . . . . . . . . . . . Polarographic Studies of Aqueous Solutions of Metal and Azide Ions. I. The Cadmium Azide Reaction. Paschoal Senise and Eduardo F . de Almeida Neves . . . . . . . . . . . Studies in Non-stoichiometry: Magnetic Susceptibilities in the Tungsten-Oxygen System. M . J . Sienko and Bireswar Banerjee . . . . . Kinetics and Products of Aquation of cis- and (ethylenediamine) - chrotrans-Dichlorobis mium(II1) Cations. David J . MacDonald and Clifford S.Garner. . . . . . . . . . . . . . Magnetic Studies of High-spin Cobaltous Compounds. VII. Some Thiocyanate Complexes. F . A . Cotton, D. M . L. Goodgame, M . Goodgame and A. Sacco . . . . . . . . . . Electronic Spectra of Some Tetrahedral Nickel(I1) Complexes. D. M . L. Goodgame, M . Goodgame and F. A. Cotton . . . . . . . Hetero-binuclear Chelates of Copper (11) and Silver (I). C. H. L i u and Chui Fan Liu . . . Complexes of Copper with Pyridine-2-aldoxime. C. H . L i u and Chui Fan L i u . . . . . . . . Malonate as a Bridging Group for Electron Transfer. George Svatos and Henry Taube . Molecular Addition Compounds of Tin(1V) Chloride. 11. Frequency and Intensity of the Infrared Nitrile Absorption in Benzonitrile Complexes. Theodore L . Brown and M . Kubota . . . . . . . . . . . . . . . . . On the Electronic Spectra of Some Substituted Benzenes. Asish Kumar Chandra . . . . . Evidence for Exchangeable Hydrogen in Chlcrophyll. J . J . Katz, M . R. Thomas, H . L. Crespi and H . H . Strain . . . . . . . . . . . . . The Concurrent Alkaline Hydrolysis and Isotopic Oxygen Exchange of a Series of p-Substituted Acetanilides. Myron L. Bender and Robert J . Thomas . . . . . . . . . . . . The Concurrent Alkaline Hydrolysis and Isotopic Oxygen Exchange of a Series of p-Substituted Methvl Benzoates. Myron L. Bender and Robert J . phomas . . . . . . . . . The Concurrent Alkaline Hydrolysis and Isotopic Oxygen Exchange of Several Alkyl Benzoates and Lactones. Myron L. Bender, Hideo Matsui, Robert J . Thomas and Stephen W . Tobey . . . . . . . . . . . . . . . . . R e a d o n of Sodium 2,6-Dimethylphenoxide with a n Ambident Electrophile: Medium Effect and Mechanism. Andrew S. Kende and Paul MacGregor. . . . . . . . . . . . . . . . The Effect of Solvent on Rates of Acid-induced Deoxymercuration. Maurice M . Kreevoy, John W . Gilje and Richard A . Kretchmer. . . Dissociation Constants of the Conjugate Acids of Substitut,ed Benzyl Phenyl Ketones and of Alkyl-substituted Benzophenones. A . Fischer, B . A . Grigor, J . Packer and J . Vaughan . . .

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Tables of Contents of ACS PUBLICATIONS Quantitative Separation of Hyperconjugation Effects frcm Steric Substituent Constants. C. Kinney Hancock, Edward A. Meyers and Billy J. Yager . . . . . . . . . . . . . . A Hammett-Taft Polar-Steric Equation for the Saponification Rates of m- and p-Substituted Alkyl Benzoates. C. Kinney Hancock and C. Paul Falls . . . . . . . . . . . . . . . Carbonium Ion Stabilization by Metallocene Nuclei. 111. Evidence for Metal Participation. E. Alexander Hill and John H. Richards On Carboxyl Activation for Peptide Synthesis. Gerassimos C. Stelakatos . . . . . . . . . . Requirements for Stereospecificity in Hydrolysis by a-Chymotrypsin. 111. The Acylamido Group. Saul G. Cohen, Yair Sprinzak and Ezra Khedouri . . . . . . . . . . . . . . Requirements for Stereospecificity in Hydrolysis by a-Chymotrypsin. IV. The Hydroxyl Substituent. Absolute Configurations. Saul G. Cohen and Ezra Khedouri . . . . . . . . . Spectroscopic Studies of a-Chymotrypsin Catalyzed Reactions. I. Spectral Changes a t 245 mp. John F. Wootton and George P. Hess . . Rauwolfia Alkaloids. XXXIX. Methyl Neoreserpate, an Isomer of Methyl Reserpate. Part 2. Mechanism of Formation. William E. Rosen and Herbert Sheppard . . . . . . . Nuclear Magnetic Resonance Spectrum of a Diastereomer of Quercitol (Deoxyinositol). Synthesis of allo-Quercitol and its 6-Chlor, 6Bromo and 6-Iodo Derivatives. J. N. Shoolery, L. F. Johnson, Stanley Furuta and G. E. McCasland . . . . . . . . . . . . . . . The Synthesis of 12~-Fluorohydrocortisone21Acetate and 12~-Chlorohhydrocortisone. Patrick A. Diassi, Josef Fried, Raymond M. Palmere and Emily F. Sabo . . . . . . . . . . Conformational Analysis. XX. The Conformation of the Acetyl Side Chain of Pregnane20-one. Norman L. Allinger and Margaret A. DaRooge . . . . . . . . . . . . . . . Ultraviolet Spectra of Several Hydro- and Functional Group Derivatives of Bicycloheptadiene Containing 7-Spiro Substituents. Charles F. Wilcox, Jr., and Rhoda R. Craig . . . . . . The Wolff-Kishner Reaction with a-Oximinoketones. Henry Rapoport and William Nilsson . . . . . . . . . . . . . . . . . Molecular Rearrangements. XIX. The Thermal Decomposition of N-Acetyl-N-nitrosoI,2,2-triphenylethylamine. Clair J. Collins, Joan B. Christie and Vernon F. Raaen . . . The Vapor Phase Reaction of 2,3-Dimethyl-2butene and Ozone. Howard E. Smith and Richard H. Eastman . . . . . . . . . . . The Mechanism of Epoxide Reactions. IV. The Reactions of Benzylamine with a Series of m- and p-Substituted Styrene Oxides in Ethanol. R. M. Laird and R. E. Parker . . . . Mechanisms of Nucleophilic Displacement in Aqueous Dimethyl Sulfoxide Solutions. Richard Fuchs, Gloria E . McCrary and Jordan J. Bloomfield . . . . . . . . . . . . . . Rearrangement of Allylic Thiobenzoates. Stanley G. Smith . . . . . . . . . . . . . . . C o m m u n i c a t i o n s to the Editor The Strengths of Cyanocarbon Acids and an HAcidity Scale for Concentrated Acid Solutions. Richard H. Boyd . . . . . . . . . . . . . Rotatory-Dispersion Changes During the Thermal Denaturation of Chymotripsinogen and Chymotrypsin. John Brandfs and Rufus Lumry . . . . . . . . . . . . . . . N-guan-Streptolidyl Gulosaminide, a Degradation Product of the Streptothricin Antibiotic Group. H. E. Carter, J. V. Pierce, G. B. Whitfield, Jr., J. E. McNary, E. E. van Tamelen, J . R. Dyer and H. A. Whaley . . . . . . . Streptothricin and Streptolin. The Structure of Streptolidine (Roseonine). H. E. Carter, C. C. Sweeley, E . E. Daniels, J. E. McNary, C. P.

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Schaffner, C. A. West, E. E. van Tamelen, J.R. Dyer and H. A. Whaley . . . . . . . . . . Constitution of the Streptolin-Streptothricin Group of Streptomyces Antibiotics. E. E. van Tamelen, J.R. Dyer, H . A. Whaley, H. E. Carter and G. B. Whitfield, Jr. . . . . . . . . The Configuration of Zr(C204) .,-I and the Stereochemistry of Discrete Eight-Coordination. J. L. Hoard, G. L. Glen and J. V. Silverton . . Bimolecular Reactions in Carbonium Ion Rearrangements. Gerasimos J. Karabatsos, Floie M. Vane and Seymour Meyerson . . . 2-Chlorocyclohexanone. Energy Calculations from Infrared Absorption Bands by Area us. Peak-Intensity Measurements. Kunio Kozima and Etsuko Hirano . . . . . . . . . Demonstration of the “Cage” Effect. Richard K. Lyon and Donald H. Levy . . . . . . . . . The Effect of Lithium Bromide on the Structural Tranhition of Ribonuclease in Solution. L. Mandelkern and D. E. Roberts . . . . . . . Distiibution of Radioactivity in Morphine from Biosynthebis with Carbon-14 Dioxide. Henry Rapoport, Naomi Levy and Frank R. Stermitz . Two Chemical Determinations of the Population of Conformations in 1,3-Butadiene. William B. Smith and John L. Massingill . . . . . . Selectivity and Mechanism of Diimide Reductions. E. E . van Tamelen, R. S. Dewey, M . F. Lease and W. H. Pirkle . . . . . . . . . .

Book Reviews Aspects of the Vitreous State. Edited by J. D. Mackenzie. Review by E. A. Flood . . . . The Hall Effect and Related Phenomena. SemiConductor Monographs. By E. H. Putley. Review by Frederick Seitz . . . . . . . . . Progresa in Semiconductors. Volume 5. Edited by A. F. Gibson, R. E. Burgess and F. A. Kroger. Reviewed by Frederick Seitz . Fatty Acids. Their Chemistry, Properties, Production and Uses. Edited by Klare s. Markley. Review by R. A. Swenson . . . . . . Technique of Organic Chemistry. Volume I. Physical Methods of Organic Chemistry. Part IV. Edited by Arnold Weissberger. Review by J . S. Waugh . . . . . . . . . .

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Scientific C o m m u n i c a t i o n s A New Approach to Lead Alkyl Analysis. Gas Phase Electron Absorption for Selective Detection. J. E. Lovelock and A. Zlatkis . . . Crushed Unfused Vycor as a Support for Gas Chromatography. L. B. Rogers and J. C. Spitzer . . . . . . . . . . . . . . . . . S y m p o s i u m on Analysis of High Polymers Resinography of High Polymers. T. G. Rochow. Chemical Structure by Absorption Spectroscopy. J. P. Luongo . . . . . . . . . . . Pyrolysis Techniques. D. A. Vassallo . . . . . Role of Carbon-14-Tagged Standards in the Analysis of Acrylonitrile-Vinyl Acetate Copolymers. M. E. Gibson, Jr., and R. H. Heidner . . . . . . . . . . . . . . . . Polymer Fractionation by Column Methods. N. S. Schneider . . . . . . . . . . . . . . Determination of Molecular Orientation in Polymer Films by Infrared Spectrophotometry. J. A. Gailey . . . . . . . . . . . . Chemical Analysis of Polymers. F. E. Crifchfield and D. P. Johnson . . . . . . . . . .

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Tables of Contents of ACS PUBLICATIONS Stability of Condensed Monolayers of Palmitic Acid on Gold. H . A. Laitinen and M . S . Chao . . . . . . . . . . . . . . . . . . 1836 Chronopotentiometry of Cerium(1V). D. G. Davis . . . . . . . . . . . . . . . . . . 1839 Direct Amperometry of Cyanide a t Extreme Dilution. J . A . McCloskey. . . . . . . . . 1842 Solution Chromatography. Summary of 14th Annual Summer Symposium Sponsored by Division of Analytical Chemistry and Held at Cleveland's Case. Institute of Technology. D. H . Wilkrns, program chairman 1644 . . . . . . . . . . . . . . . . . . . . Quantitative Gas-Liquid Chromatography of Short-Chain Fatty Acids as 2-Chloroethanol . . 1847 Esters. Kurt Oette and E . H . Ahrens, J r . Gas Chromatographic Determination of Sulfur Compounds in Naphthas Employing a Selective Detector. P. J . Klass . . . . . . . . 1851 Identification of Polyhydric Alcohols in Synthetic Resins by Programmed Temperature Gas Chromatography. G. G. Esposito and M . H . Swann . . . . . . . . . . . . . . 1854 Separation and Determination of Mono- and Dinitrotoluene Isomers by Gas-Liquid chromatography. J . S. Parsons, S. M . Tsang, M . P . DiGiarmo, Raymond Feinland, and R. A. L. Paylor . . . . . . . . . . . . . 1858 Gas Chromatography of Steroids. Relation of Structure of Molar Response in an Argon Ionization Detector. C. C. Sweeley and T.-C. L o Chang . . . . . . . . . . . . . . . . 1860 Quantitative Paper Chromatography of Plasma Amino Acids. Modification of the Dinitrophenylation Procedure of Levy. Carl Peraino a n d A . E . Harper . . . . . . . . . . . . . 1863 Improved Sampling and Recording Systems in Gas Chromatography-Time-of-Flight Mass Spectrometry. A . A. Ebert, Jr. . . . . . . 1865 Resolution of Cyclopentanes and Cyclohexanes in Gasolines by Mass Spectrometry. H . E . Howard and W. C. Ferguson . . . . . . . . 1870 Dehydrogenation as an Aid to the Mass Spectrometric Analysis of Naphthenes. L . R . Cousins,D . J . Clancy, and G. F. Crable . . . . . . 1875 Determination of ,Vanadium and Free Radical Concentrations in Crude Petroleum by Electron Magnetic Resonances. E . M . Roberts, R . L. Rutledge, and A. P . Wehner . . . . . . 1879 Determination of Nonamines in High Molecular Weight Fatty Amines. J . P. Nelson, L. E . Peterson, and A. J . Milun . . . . . . . 1882 Polymer Distribution in Alkyl Polyoxyethylene Condensates. Determination of Monomer through Tetramer. M . E . Puthoff and J. H . Benedict . . . . . . . . . . . . . . . . 1884 Titrimetric Method for Continuous Determination of Carbon Dioxide and Its Application in Amino Acid Chemistry. Abraham Patchornik and Yechiel Shalitin . . . . . . . 1687 Photolytjc Determination of Trace Amounts of Organic Material in Water. James Beattie, Clark Bricker, and David Garvin . . . . . . 1890 Photometric Titration of Certain Aldehydes with Sodium Borohydride. Evelyn Cochran and C. A. Reynolds . . . . . . . . . . . . 1893 Voltammetric Studies of Phenol and Aniline Ring Substitution. J . C. Suatoni, R. E . Snyder, and R. 0.Clark . . . . . . . . . . 1694 Determination of Homolog Distribution of Mixed Alkylbenzyldimethyl Ammonium . . . . . 1898 Chlorides. H . P . Warrington,J r . Reactivity of Some Hydroxyketones with Blue Tetrazolium. P . E. Manni and J. E. Sinsheimer . . . . . . . . . . . . . . . 1900 A System for Identification of Barbiturates in Blood. G. W. Stevenson . . . . . . . . . 1903 Simple Procedure for Conversion of Oxygen of Orthophosphate or Water . to . Carbon Dioxide for Oxygen-18 Determinatlon. P .

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D. Boyer, D. J . Graves, C. H . Suelter, and M . E . Dempsey . . . . . . . . . . . . . Improved Methods of Using the Thermobalance to Determine Thermal Stabilities. J . R . Soulen and Isadore Mockrin . . . . . . Determination of Trace Sulfur in Leaded Gasoline by Modified Lamp-Turbidimetric Method. R. W . K l i p p . . . . . . . . . . New Fire Assay Method for the Determination of Gold. G. H . Faye and W . R. Inman . . . . Evaporation of Boron from Acid Solutions and Residues. Cyrus Feldman . . . . . . . . . Steady-State Distribution. New Instrument for Continued Batchwise Separation by Extraction. F. C. Alderweireldt. . . . . . . Spectrophotometric Determination of Polyvinyl Alcohol in Paper Coatings. J . H . Finley . . . . . . . . . . . . . . . . . . Spectrophotometric Determination of Highly Functional Organic Acids with cis-Dichlorobis (Ethylenediamine) Chromium(II1) Chloride. Satoru Egashira . . . . . . . . . Spectrophotometric Determination of Thorium with Solochromate Fast Red. Johann Korkisch and G. E . Janauer . . . . . . . . . . Spectrophotometric Determination of Cobalt V. D . Anand, with Thioglycolic Acid. G. S. Deshmukh, and C. M . Pandey . . . . . . Spectrophotometric Determination of Traces of Iron with 4,7-Diphenyl- 1,lo- phenanthroline. Application to Vanadium, Chromium, Titanium, Niobium, Tantalum, Uranium, Tungsten Metals, Alloys, and Compounds. A. R. Gahler, R. M . Hammer, and R. C. Shubert . . . . . . . . . . . . . . . . . Simultaneous Spectrophotometric Determination of Copper, Cobalt, Nickel, and Chromium. V. K. Gustinand T. R. Sweet. . . . . Gravimetric Determination of Sodium and Potassium with N,N,-Dialkylethanolammonium Orotates. Renato Selleri and Oreste Caldini . . . . . . . . . . . . . . . . . Precipitation of Barium Sulfate from Homogeneous Solution Using Complexation and Replacement. F. H. Firsching . . . . . . . Determination of Powder Moisture by Azeotropic Distillation and Near-Infrared Spectrophotometry. Hans Brandenberger and Heinz Bader . . . . . . . . . . . . . . . Rapid Microdetermination of Scandium and Dysprosium in Rare-Earth-Rich Materials by Neutron Activation and Gamma-Ray Spectrometry. Minoru Okada . . . . . . . . . Cathodic Action of the Lead-Glutamate Complex a t the Dropping Mercury Electrode. T.-T. Lai and T.-L. Chang . . . . . . . . . Polarographic Method for Determination of Chlorbutol. J a n Birner . . . . . . . . . .

Correspondence Modified Iodometric Method for Semimicro Determination of Lipid Peroxides. L. K. Dahle and R. T . Holman . . . . . . . . . Flame Spectrophotometric Study of Yttrium. W. J . Carnes and J . A. Dean . . . . . . . Lead Determination Using an Anion Exchanger and Sodium Chloranilate. E . A . W y n n e and R. D. Burdick . . . . . . . . . . . . Ultrasonic Method for Fluorescence Determination of Phthalates. Alfred Weissler and Barbara Wasileski . . . . . . . . . . . . Volumetric Determination of Tungsten in Steel C. L. Luke. . . . . . . . . . . . . . . . New Plotting of the B E T Method. Tominaga Keii, Tokuji Takagr, and Setsuko Kanetaka

1906 1909 1912 1914 1916 1920 1925

1928 1930 1933

1937 1942

1944 1946

1947

1949 1953 1955

1960 1961 1963 1963 1964 1965

Aids Micro Cell for Voltammetry with the Hanging Mercury Drop Electrode. W . L. Underkofler and Irving Shain . . . . . . . . . . . . . 1966

Spectrometry Nomenclature

. . . . . . .

1968

Tables of Contents of ACS PUBLICATIONS

Journal of

AGRICULTURAL AND FOOD CHEMISTRY November/December 1961, Vol. 10, No. 6 Food Processing Stilbestrol Effects on Meats, Influence of Orally Administered Stilbestrol on Connective Tissue of the Skeletal Muscle of Lambs Fed Varying Levels of Protein. E . N . McIntosh, D. C. Acker. and E. A . Kline . . . . . . . . . . Meat Tenderness Factors, Determination of Mucoprotein in Skeletal Muscle. E . N. McIntosh . . . . . . . . . . . . . . . . Interfacial Energies in Milk, Influence of Milk Proteins on Interfacial Tension between Butter Oil and Various Aqueous Phases. R. H . Jackson and M . J . Pallansch . . . . . . . . Browning Reaction in Wheat Germ, Changes in Dye Absorption Capacity of Wheat Embryos Undergoing a Browning Reaction. Y . J . Pomeranz and J. A . Shellenberger . . . . . . Food Processing/Nutrition Radiation Sterilization of Foods, Comparison of the Radiosensitivities of the Fat-soluble Vitamins by Gamma Irradiation. F. W . Knapp and A. L. Tappel . . . . . . . . . . . . . Plant Protein Constituents, Hydroxyproline Content of Seed Meals and Distribution of the Amino Acid in Kernel, Seed Coat, and Pericarp, C. H . V a n Etten, R. W . Miller, F. R . Earle, I.A . Wolfe, and Q. Jones . . . . . . . . . . . . Thiamine in Soybean Meal, The Alleged “Thiamine-Destroying Factor” in Soybeans. F. B. Weakley, A . C. Eldridge, and L. L. McKinney . Quality and Flavor of Dairy Products, Review of the Biochemical Properties of Milk and Lipid Deterioration in Milk and Milk Products as Influenced by Natural Varietal Factors. V. N . Krukovsky . . . . . . . . . . . . . . . .

418 421

420

428

430

468

469

478

481

484 488

The Journal of

PHYSICAL CHEMISTRY 433

October 1961, Vol. 65, No. 10 435

439

Food Processing/Ferment ation Feed Additives, Microbiological Production of Carotenoids. Stabilization of p-Carotene in Dried Fermentation Solids. A. Ciegler, G. E . N . Nelson and H. H . Hall . . . . . . . . . 447 Ferment ation Oxalate in Beer, The Rapid Enzymatic Determination of Oxalate in Wort and Beer. G. J . Haas and A . I . Fleischman . . . . . . . . . Plant Nutrients and Regulators Nitrogen Fertilizers, Hydrolysis, Nitrification, and Nitrogen Availability of Oxamide, as Influenced by Granule Size. J . D. DeMent, C. M . Hunt, and G. Stanford . . . . . . . . . . . Fertilizer Technology, Pilot Plant Study of an Ammonium Fluoride Process for Recovery of Fluorine from Superphosphate. F . G. Heil, R. D. Young, and J . J . Stump . . . . . . . . . Plant Tissue Analysis, Chelometric Titration of Calcium and Magnesium in Plant Tissue. Method for Elimination of Interfering Ions. R. M . Carlson and C. M . Johnson . . . . . . Role of Silica in Plants, Absorption and Deposition of Silica by Four Varieties of Sorghum. F . C. Lanningand Y . Linko . . . . . . . .

Pesticides Pesticide Residues, Modified and Improved Procedure for Schoniger Total Chlorine Residue Analysis. L.E . St. John, Jr., and D. J . Lisk . Insecticide Residues, Determination of Residues of Phorate and its Insecticidally Active Metabolites by Cholinesterase Inhibition: Part I. The Basic Method. Part 11. Alternative Sample Preparation, and Recovery Data. A . N . Curry, L. M . Kress, and R. A . Paylor . . Insecticide Residues, A Procedure for the Microdetermination of 1-Butoxy-2-(2-Thiocyanoethoxy) Ethane (Lethane 384) with Applications for Determination of Residues in Milk and Animal Tissues. C. F. Gordon, L . D. Haines, and A . L. Wolfe . . . . . . . . . . . . . Insecticide Residues in Milk, D D T Residues in Milk from Dairy Cows Fed Low Levels of D D T in Their Daily Rations. G. Zweig, L. M . Smith, S. A . Peoples, and R. Cox . . . . . . Insecticide Effects on Animals, The Response of Experimental Animals to Phosdrin Insecticide in Their Daily Diets. F. P. Cleveland and J . F. Treon.. . . . . . . . . . . . . . . . . Herbicide Residues, Microdiffusion Separation and Determination of Microgram Quantities of Thiocyanate in Corn. H. S. Sigal . . . . .

451

453

45 7

460 463

Plant Regulators/Pesticides Growth Regulator Determination, Quantitative Determination of 3-Amino-1,2,4-triazole. R . A . Herrett and A . J , Linck . . . . . . . . 466

35th NATIONAL COLLOID SYMPOSIUM, University of Rochester, Rochester, New York, June 14-16, 1961 The Chemisorption of Gases on Cobalt Oxide Surfaces at Low Temperatures. D . S. MacIver and H. H . Tobin . . . . . . . . . . . A Comparison of Integral Ehthalpies, Free Energies and Entropies of Adsorption. J . I. Chessick and A . C. Zettlemoyer . . . . . . . Thermodynamic Properties of Water Adsorbed on Quartz. J . W . Whalen . . . . . . . . Heats of Immersion. V. The Ti02-H20System -Variations with Particle Sizes and Outgassing Temperature. W. H. Wade and H. Hacker man . . . . . . . . . . . . . . . The Adsorption of Oil-Soluble Sulfonates at the Metal/Oil Interface. Willard D. Bascom and C. R. Singleterry . . . . . . . . . . . Thermal Forces on Aerosol Particles. C. F. Schadt and R. D. Cadle . . . . . . . . . . Further Studies on the Sorption of H20 and DzO Vapors by Lysozyme and the Deuterium Wasyl S. -Hydrogen Exchange Effect. Hnojewyj and Lloyd H. Reyerson . . , . , , The Effect of Vapors on Monolayer Permeability to Carbon Dioxide. Martin Blank . . . . . Mechanism of the Selective Flux of Salts and Water Migration through Non-aqueous Liquid Membranes. Henri L. Rosano, Paul Duby andJackH.Schulman . . . . . . . . . . The Diffusion Time-Lag in Porous Media with Dead-End Pore Volume. Richard C. Goodnight and Irving Fatt . . . . . . . . . . . Light Scattering Functions for m = 1.60 (0.04) 2.08 and 01 = 0.1 (0.1) 10.0 I. Mie Scattering Coefficients. M . Kerker, J . P. Kratohuil and E . Matijeuic . . . . . . . . . . . . . VOL. 53, NO. 12

1665 1672 1676

1681 1683 1689

1694 1698

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DECEMBER 1961

103 A

Tables of Contents of ACS PUBLICATIONS Melting Kinetics of Quartz and Cristobalite. N. G. Ainslie, J . D. Mackenize and D. Turnbull . . . . . . . . . . . . . . . . . . Adsorption of Thorium Ions on Silver Iodide Sols. E. Matijeuic, M . B . Abramson, R. H . Ottewill, K . F. and M . Kerker . . . . . . . Modification of Growth Rate and Habit of Adipic Acid Crystals with Surfactants. Alan S. Michaels and Frederick W . Tausch, Jr. . . The Origin of Spherulites. Gerald W . Sears . . Crystallization of Poly- (ethylene oxide) in Bulk. Wilson J . Barnes, William G. Luetzel and Fraser P . Price. . . . . . . . . . . . . . An Optical Diffractometer Analysis of Light Scattering Patterns Obtained for Polyethylene Films. Philip R. Wilson, S . Krimm, and Richard S. Stein . . . . . . . . . . . . . Countercurrent Distribution of Chemically Reacting Systems. 11. Reactions of the Type A B ~ t C. . J. L. Bethune and Gerson Kegeles . . . . . . . . . . . . . . . . . Countercurrent Distribution of Chemically Reacting Systems. 111. Analogs of Moving Boundary Electrophoresis and Sedimentation. J . L . Bethune and Gerson Kegeles . . . . . Polycation-Polyanion Complexes: Preparation and Properties of Poly- (vinylbenzyltrimethylammonium) - Poly - (styrenesulfonate) Alan S. Michaels and Richard G. Miekka . . Critical Phenomena in Aqueous Solutions of Long Chain Quaternary Ammonium Salts. 11. Specificity and Light Scattering Properties. Irving Cohen and Tony Vassiliades . . Critical Phenomena in Aqueous Solutions of Long Chain Quarternary Ammonium Salts. 111. Viscosity, Diffusion and Charge Properties. Irving Cohen and Tony Vassiliades . . Ultracentrifugal Determination of the Micellar Character of Non-Ionic Detergent Solutions. 11. C. W . Dwiggins, Jr. and R . J . Bolen . . Colloidal Alumina-The Chemistry" and Morphology of Colloidal Boehmite. John Bugosh . . . . . . . . . . . . . . . . . Casein Interactions and Micelle Formation. David F. Waugh . . . . . . . . . . . . . Phase Separation in Polyelectrolyte Solutions. 11. Interaction Effects. Arthur Veis . . .

+

Some Colloidal Properties of Decyl- and DOdecyltrimethylammonium Dodecyl Sulfate. Horst W . Hoyer, Anne Marmo and Margaret Zoellner . . . . . . . . . . . . . . . . The Electrophoretic Mobilities and Critical Micelle Concentrations of the Decyl-, Dodecyl- and Tetradecyltrimethylammonium Chloride Micelles and their Mixtures. Horst W. Hoyer and Anne Marmo . . . . . . . . Water Sorption by Dextrans and Wheat Starch a t High Humidities. N . W . Taylor, J . E . Cluskev and F. R . Senti . . . . . . . . . . Deuterium Exchange in Starches and Amylose. N. W . Taylor, H . F. Zobel, Milford White and F.R.Senti . . . . . . . . . . . . . . . Kinetics of Ion Exchange in a Chelating Resin. Richard Turseand Wm. Rieman III . . . . The Starch-Iodine-Iodide interaction. 11. Potentiometric Investigations. John A. Thoma and Dexter French . . . . . . . . . . . . Solvents Having High Dielectric Constants. XI. Electromotive Force Measurements of the Cell Pt, Hz; H C l ( F ) ; AgC1-Ag in NMethylacetamide at 40 . Lyle R. Dawson, Richard C. Sheridan and Hartley C. Eckstrom . Deuterium Isotope Effects in the Gas. Phase Oxidation of Formaldehyde by Nitrogen Dioxide. Donald Barton . . . . . . . . . Solution Conductance of Cyanocarbon Salts. Richard H. Boyd . . . . . . . . . . . .

1 04 A

INDUSTRIAL AND ENGINEERING CHEMISTRY

1718 1724 1730 1738 1742

1749

1755

1761

1765

1774

1781

1789 1793 1798

1804

1807 1810

1816 1821 1825

1829 1831

1834

The Kinetics and Mechanism of the Thermal Decomposition of Plutonium Hexafluoride. J . Fischer, L. Trevorrow and W . Shinn . , , 1843 The Heats of Combustion of Niobium Carbides. Elmer J . Huber, Jr., Earl L . Head,,CharEes E. Hollev, . 1846 - . E. K. Storms and N. H. Krakorian Kinetics of the Reaction of Sulfur Tetrafluoride with Uranium Trioxide and Uranyl Fluroide. Carl E. Johnson and Jack Fischer. . . . . . Cation Hydration Effects on the Thermodynamics of Water Adsorption by Kaolinite. J. J. Jurinak and D. H. Volman . . . . . . Actinide(1V) Chloride Species Absorbed by Anion Exchange Resins from Chloride Solutions. J . L. Ryan . . . . . . . . . . . . Alumina: Catalyst and Support. XII. The Effect of Intrinsic Acidity of Aluminas upon Herman Hydrogen-Deuterium Exchange. Pines and Jean Ravoire . . . . . . . . . . Ethane Radiolysis a t Very Low Conversion. Kang Yang and Preston L. Gant . . . . . . Electromotive Force Measurements in the System AgNOq and NaCl in Equimolar NaN08-KN0, Mixtures and their Comparison with the Quasi-Lattice Theory. D. G. Hill and M . Blander . . . . . . . . . . . . . Spectrophotometric Determination of the Dissociation Constant of Silver Chloride in Stanley Bruckenstein and Jiro Pyridine. Osugi . . . . . . . . . . . . . . . . . Exact Nuclear Magnetic Resonance Shielding Constants for Hydride, Helium, Lithium Oxygen(V1). R. E. Glick . . . . . . . . . Exploratory Studies on the Surface Activity, of Polysoaps. Helmuth E . Jorgensen and Ulrich P. Strauss . . . . . . . . . . . . . . . Separation of Nitrogen and Oxygen Isotopes by Exchange of Nitric Oxide with Non-aqueous Solutions of Nitric Oxide Complexes. A . Nartan and T . I . Taylor . . . . . . . . . Proton Magnetic Resonance Study of the Basicity of the Silicon-Oxygen Bond. Charles M . Huggins . . . . . . . . . . . . . . . Critical Composition in Liquid Mixtures of Components of Very Different Molar Volumes. Kdz6 Shinoda and Joel H. Hildebrand . . . . Catalytic Activity of the Lanthanide Oxides for for the Dehydrogenation of Cyclohexane. C. B . McGough and G. Houghton . . . . . .

Notes The Rate of Electron Transfer between the Tris - (ethylenediamine) - cobalt(I1) and Cobalt(II1) Ions. Francis P . Dwyer and Alan M . Sargeson . . . . . . . . . . . . . . . Conformation of Fluorinated Cyclohexanes. J. Feeney and L. H . Sutcliffe . . . . . . . . Diastereoazeotropes as a Means of Resolution. Clifford J. McGinn . . . . . . . . . . . . The Reaction between Uranium(1V) and Hydrogen Peroxide. F. B . Baker and T . W . Newton. . . . . . . . . . . . . . . . . . . Tetrachlorophthalic Anhydride-Azahydrocarbon Complexes. Mihir Chowdhury . . . . . Enthalpies and Entropies of Formation of Mercury(I1)-Halide 1:1 Complex Ions. G. N. Malcolm, H. N . Parton and I . D. Watson

1849 1853 1856

1859 1861

1866

1868 1871 1873

1877 1881 1885 1887

1892 1894 1896 1897 1899

. . . . . . . . . . . . . . . . . . . . 1900 Proton Magnetic Resonance of Glycylglycinate, Glycineamide, and their Metal Complexes. Norman C. L i , LeRoy Johnson and James Shoolery . . . . . . . . . . . . . . . . 1902 The Electric Moments of Some Nitrate Esters. A. R. Lawrence and A. J . Matuszko . . . . 1903 Hydrated and Anhydrous Bisethylenediamine Copper(I1) Sulfate. L. V . Gregor, J . J . Fritz and P . E. Field . . . . . . . . . . . . . 1904

Tables of Contents of ACS PUBLICAT The Effect of Campper Alkanoates on Oxidizing Olefins. P . W . Allen . . . . . . . . . . . 1906 Photochrom. Carl A . Heller, Dwight A. Fine and Ronald A . Henry . . . . . . . . . . . 1908 Determination of' the Ionization Constants of Some Phenylniercury Compounds. S. S . Parikh and Thomas R. Sweet . . . . . . . . 1909 Sorption of Sulfur Hexafluoride by Artificial Zeolites. Daniel Berg and William M . Hickam 1911 . . . . . . . . . . . . . . . . . . . . The Heat of Formation of C2f. Leo Brewer, John L. Margrave, Richard F. Porter and Karl Wieland . . . . . . . . . . . . . . . . 1913 Reactio? of Atomic Hydrogen with Solids at -195 Vincent J . CeCarlo and F. 0. Rice . 1913 Studies of the Copper(I1)-Alanine and Phenylalanine Systems in Aqueous Solution. Dissociation and Formation Constants as a Function of Temperature. R. M . Izatt, J . W. Wrathall, and K . P. Anderson . . . . . . 1914 Proton Nuclear Magnetic Resonance Spectroscopy. XII. Tetramethylsilane: Some Observations Concerning Line Width and Line Shape. George V a n Dyke Tiens . . . . . . 1916 The Heat Content and Heat Capacity of Boron R. A . McNitride from 298 to 1689'K. Donald and D . R. Stull . . . . . . . . . . 1918

.

Communications to the Editor Electron Spin Resonance of Aromatic Hydrocarbons on Silica-Alumina Catalysts. James K . Fog0 . . . . . . . . . . . . . . . . 1919 The Influence of X-Rays on Catalytic Activity as Related to Incorporated Radioactivity. Norman A . Krohn and Hilton A. Smith . . . 1919

Journal of

ORGANIC CHEMISTRY October 1961, Vol. 26, No. 10 Studies of Configuration. XI. A New Method for the Evaluation of Conformational Free Energy Differences Donald S. Noyce and Lloyd J. Dolby . . . . . . . . . . . . . . Conformational Analysis. XVIII. The Relative Stabilities of the cis and trans A/B Ring Junctures of Steroidal 4 and 6 Ketones. Norman L. Allinger, Margaret A . Da Rooge, and Robert B. Hermann . . . . . . . . . . . . Stereochemistry of the Cyclization of the HalfEsters of Diarylitaconic Acid. E . E . Smissman, P . S. Portoghese, and R. A . Mode . . . . The ortho-Claisen Rearrangement. V. The Products of Rearrangement of Allyl m - X Phenyl Ethers. William N . White and Carl D. Slater . . , . . , , , . , . , . , , , , . Molecular Rearrangement of Diazotized o-Aminophenylcarbinols. Martin Stiles and Anthony J . Sisti . . . . . . . . . . . . . . . . . . Investigation of Methods for Preparing Pure Secondary Alkyl Halides. James Cason and John S. Correia . . . . . . . . . . . . . . Selective ortho and meta Migration of a n Acyl Group in the Fries Rearrangement of Creosol Esters. Paolo Da Re and Luigi Cimatoribus . . The Fries Reaction of 2,4-Dichlor0-5-methylphenyl Acetate. S. E . Cremer and D . S. Tarbell . . . . . . . . . . . . . . . . . . . Thermal Isomerization of Hydroborated Olefins. T . J . Logan . . . . . . . . . . . . . . . The Neutral Solvolysis of the Aspirin Anion in Aqueous and Mixed Solvents. Edward R. Garrett . . . . . . . . . . . . . . . . . The McFadyen-Stevens Reduction in the Alipha.tic Series. Milon Sprecher, Malka Feldkimel, and Meir Wilchek . . . . . . . . . .

3619

3626 3628

3631 3639 3645 3650 3653 3657 3660 3664

The Chemistry of p-Bromopropionyl Isocyanate. IV. Elimination Reactions of Some p-Bromopropionic Acid Derivatives. Harry W . Johnson, Jr., and Martin Schweitzer . . . . . . . . . . . . . . . . . . . 3666 Cyclopropanes Derived from Diaryldiazomethanes. I. Amino Alcohols of the cis Series. Richard Baltzly, Nariman B . Mehta, Peter B. Russell, Ronald E . Brooks, Eugene M . Grivsky, and Anne M . Steinberg. . . . . . . . . . . 3669 Hydrogenolysis of Metal Hydrides. 111. Hydrogenolysis of Alkylallylarylamines by Lithium Aluminum Hydride. Virgil L. Tweedie and John C. AllabashL . . . . . . . . . . . 3676 Ammonolysis of Vicinal Acetoxy Chlorides. S. J . Lapporte and L. L . Ferstandig . . . . . . 3681 Interaction of an Ivanov and an Ivanov-Like Reagent with 7-Butyrolactone and r-Valerolactone. F. F. Blicke and B . A. Brown . . . . 3685 The Base-Catalyzed Self-Condensation of a,pUnsaturated Ketones. Condensation of Cyclopropyl Methyl Ketone with 2-Methylpropanal to Isomeric Diketones, C18H180%.Arnold T. Nielsen, Donald W . Moore, and Kristin Highberg . . . . . . . . . . . . . . . . 3691 Alkylations a t the a-Carbon of Phenylacetamide and Phenylacetic Acid through Their Disodio Salts. Robert B . Meyer and Charles R . Hauser . . . . . . . . . . . . . . . . . 3696 Condensation of o-Phthalaldehyde with Ketones. I. The Formation and Structures of Some 4,5-Benztropones. W . Davey and H. Gottfried 3699 Condensation of o-Phthalaldehyde with Ketones. 11. W . Davey and H . Gottfried . . . . . . . 3705 Reaction of t-Ethinyl Alcohols with Aryl ISOcyanates. Seymour L. Shapiro, Victor Bandurco and Louis Freedman . . . . . . . . . 3710 The Vinylation of Glycerol. Norman Shachat, Henry J. Schneider, John J . Nedwack, Guy C. Murdoch, and James J . Bagnell . . . . . . . 3712 Behavior of Halogenated Nitrobenzenes with p-Diketones. 11. 6-Nitroanthranil from 2,4Dinitrophenylacetone. S. S. Joshi and I . R . Gambhir . . . . . . . . . . . . . . . . . 3714 Syntheses Pertaining to the Carbamoylation of Cyclic 1,3-Dicarbonyl Compounds with Urea. Homer C. Scarborough . . . . . . . . . . . 3717 The Reaction of Urea with Cyclic 1,3-Dicarbonyl and Other Active Hydrogen Compounds. Homer C. Scarborough and William A . Gould . . . . . . . . . . . . . . . . . . 3720 Direct Preparation of Benzyllithium and a-Methylbenzyllithium in Tetrahydrofuran. Henry Gilman and Herbert A. McNinch. . . . 3723 The Synthesis of AS79- and ~!,~,'~-Octal-l-one. Herbert 0. House and Hugh W . Thompson . . 3729 Synthesis of 1,2,3,4-Tetramethylcyclopentanes. I. Harold N. Miller and Kenneth W . Greenlee 3734 Aryl Norbornane Derivatives. I. Preparation of Compounds. Donald C. Kleinfelter and Paul V o n R. Schleyer . . . . . . . . . . . 3740 Ester Formation in the Hydrogen FluorideCatalyzed Reaction of Olefins with Carbon Monoxide. B. S. Friedman and S . M . Cotton 3751 A New Synthesis of Phenylglyoxal Acetals. David T. Manning and Harry A , Stansbury, Jr. . . . . . . . . . . . . . . . . . . . 3755 Some Esters of 1,2,4-ButanetricarboxylicAcid. J . W . Lynn, R. L. Roberts, and S . W . Tinsley . 3757 Enamines of 2-Indanones. Alfred T. Blomquist and Emil J . Moriconi . . . . . . . . . . . 3761 A New Synthetic Route to a-Isonitrosoacetonitriles. The Chlorination of Isonicotinaldehyde Oxime. Edward J. Poziomek and Arthur R. Melvin . . . . . . . . . . . . . . . . . 3769 Hindered Amines. Preparation and Reactions of Some Secondary Acetylenic Amines. Nelson R. Easton, Robert D. Dillard, Wilbur J . Dofan, Mabel Liuezey, and Dwight E . Morrison . . . . 3772 VOL. 53, NO. 12

DECEMBER 1961

105 A

Tables of Contents of ACS PUBLICATIONS Highly Hindered Aliphatic Tertiary Amines. C. Ainswirth and Nelson R. Easton. . . . . . 3776 Some S-Substituted Derivatives of 2-Aminoethanethiol. Thomas P. Johnston and Anne Gallagher . . . . . . . . . . . . . . . . 3780 The Preparation and Reactions of 1-Cyanoformimidic Acid Hydrazide. Ken Matsuda and Lucille T. Morin . . . . . . . . . . . . . 3783 A New Synthesis of Amino Acids. 111. The Preparation of dl-Glutamic Acid by the Michael Reaction of Acetamidomalonic Acid and Acetamidocyanoacetic Acid Derivative with. Acrylic Acid Derivative in Liquid Ammonia. Kotaro Shimo and Shigeru Wakamatsu . . . . . . . . . . . . . . . . . . 3788 Azo Coupling in the Pyrrole S stem. The Synthesis of Azopyrroles. A&ed Kreutzberger and Paul A. Kalter . . . . . . . . . . . . 3790 Pyridine 1-Oxides. IX. Further Oxidative Dimerizations of 4-Nitro-3-picolines. Edward C. Taylor and John S. Driscoll . . . . . . . . . 3796 Amine Oxides. A Comparison of 2-Vinylpyridine N-Oxide and the 2,3-Dihydroisoxazolo[2,3-a]pyridinium Ion. V. Boekelheide and Roland Scharrer . . . . . . . . . . . . . . 3802 Reductions with Ruthenium. 11. Its Use in the Hydrogenation of Pyridines. Morris Freifelder and George R. Stone . . . . . . . . . . . . 3805 2-Alkyl(aryl)- and 2,7-Dimethyl-4-substituted Aminopyrrolo [2,3d]pyrimidines. R. A. West and L. Beauchamp . . . . . . . . . . 3809 Indenoquinolines. I. Derivatives of 11HIndeno [1,2-b ]quinoline. Norman H . Cromwell and Ronald A. Mitsch . . . . . . . . . . 3812 Indenoquinolines. 11. Derivatives of 6H-Inden0 [Z,l-b]quinoline. Norman H. Cromwell and Ronald A. Mitsch . . . . . . . . . 3817 Periodate Oxidations of Oxazolines. H. L. Wehrmeister . . . . . . . . . . . . . . . 3821 Synthesis of 5-0xo-2-pyrazoline-4-carboxaldehydes. David J. Wallace and James M. Straley . . . . . . . . . . . . . . . . . 3825 Phenoxazines. 11. 10-Dialkylaminoalkylphenoxazines. Hubert Vanderhaeghe and Lucien Verlooy . . . . . . . . . . . . . . . . . 3827 A Synthesis of Thyronamine and its Lower Homolog. L. Petit and N. P. Buu-Hoi’ . . . . 3832 The Structure o€ Certain Polyazaindenes. IX. Sensitivity of the Ultraviolet Absorption Spectra t o p H Variation, and Amine Salts of Tetrazaindenes. M. A. Hill, G. A . Reynolds, J. F. Tinker, and J. A. Van Allan . . . . . . . . 3834 Purine Nucleosides. 11. The Preparation of 6-Substituted 9- (Tetrahydro-2-fury1)purines and 6-Substituted 9- (Tetrahydro-2-thieny1)purines as Models of Purine Deoxynucleosides. Leland R. Lewis, F. Howard Schneider, and Roland K. Robins . . . . . . . . . . . . . . 3837 3-Substituted Dihydrobenzothiadiazine 1,LDioxides as Diuretic Agents. John G. Topliss, Margaret H . Sherlock, Frank H. Clarke, Maria C. Duly, Berit W. Pettersen, Janet Lipski, and Nathan Sperber. . . . . . . . . . . . . . 3842 Thyroxine Analogs. I. Methylated Thyroformic Acids. Earle Van Heyningen . . . . . . 3850 Potential Curare-Like Compounds Derived from Bisdialkylaminoalkyl Esters of Some 3-Phenylglutaric Acids. Walter T. Smith, Jr., and John W.Ryan . . . . . . . . . . . . . . . . 3856 Synthesis of Potential Anticancer Agents. V. Schiff Bases and Related Compounds. Frank D. Popp and Warren Kirsch . . . . . . . . 3858 Potential Carcinostatic Derivatives of Benzo [a]and Benzo [b Iphenoxazine. Kalyanmay Sen and David A. Shirley . . . . . . . . . . . 3861 Synthesis of Potential Anticancer Agents. XI. Synthesis and Reactions of Derivatives of 6-Methyluracil-5-sulfon1c Acid. Robert C. Elderfield and Raj N. Prasad . . . . . . . . . 3863

106 A

INDUSTRIALAND ENGINEERINGCHEMISTRY

The Oxidation and Acid Isomerization of Bacitracin A. William Konigsberg, R. J. Hill, and Lyman C. Craig . . . . . . . . . . . . 3867 Studies on the Synthesis of Polypeptides. Bradykinin. E, D. Nicolaides and H. A. De Wald . . . . . . . . . . . . . . . . . . 3872 The Preparation of 6-Methoxycorticoids. Milton Heller and Seymour Bernstein . . . . . . . . 3876 An Optical Rotatory Dispersion Study of Side Chain Epimers in the Pregnane Series. William A. Struck and Ronald L. Houtman . . . . 3883 The Synthesis of 16~~-Fluoromethyl Steroids. P. F. Beal and J. E. Pike . . . . . . . . . . 3887 Degradation of Corticosteroids. IV. Preparation of 3,5-Seco-4-nor-6-androstene-5,11,17trione-3-oic Acid and 3,5-Seco-4-nor-llp-hydroxyandrostane-5,17-dione-3-oicAcid 3,11Lactone. E . Caspi, (Mrs.) Badar Taqui Khan, and W. Schmid . . . . . . . . . . . . . . 3894 Degradation of Corticosteroids. V. Preparation and Certain Reactions of 11-Oxygenated-3,5seco-4-nor-5p-hydroxy-3-oic Acid 3,5-Lactones. Eliahu Caspi, Walter Schmid, and (Mrs.) Badar Taqui Khan . . . . . . . . . 3898 Studies in the Total Synthesis of Steroids and Their Analogs. I. Synthesis of 19-Nortestosterone. Leland J. Chinn and Hugh L. Dryden, Jr. . . . . . . . . . . . . . . . . . 3904 Studies in the Total Synthesis of Steroids and Their Analogs. 11. Des-A Analogs of Clinically Active Steroids. Leland J. Chinn, Hugh L. Dryden, Jr., and Robert R. Burtner . . . . 3910 The Synthesis of Certain 7a-Alkylthio and 7aAcylthio Steroid Hormone DeSivatives. Robert E . Schaub and Martin J. Wem . . . . . . 3915 Enol Ethers of Steroidal A4-3-Ketones. A. L. Nussbaum, E. Yuan, D. Dincer, and E. P. Oliveto, . . . . . . . . . . . . . . . . . 3925 The Acid Epimerization of D-Glucose. Yasuo Ohno and Kyle Ward, Jr. . . . . . . . . . . 3928 Debenzyloxycarbonylation of 1,3,4,6-Tetra0 - acetyl 2 benzyloxycarbonylamino - 2deoxy-D-hexopyranoses in the Conversion of a,p-Acetoxy to Glycosyl Bromide. Konoshin Onodera and Tohru Komano . . . . . . . . 3932 The Synthesis of Certain Benzylidene Derivatives of &Ribose and Ribitol. D. J. J. Potgieter and D. L. MacDonald. . . . . . . . . 3934 Partial Esterification of 1,6-Anhydro-p-n-glucopyranose. Roger W. Jeanloz, Annette M. C. Rapin, and Sen Itiroh Hakomori . . . . . . . 3939 6,6 -Diglycose Anhydrides. Roy L. Whistler and Armin Frowein. . . . . . . . . . . . . . 3946 Organic Sulfur Compounds. IV. Some Addition and Co-oxidation Reactions of 4-Chlorobenzenethiol with Dicyclopentadiene and Aldrin. Alexis A. Oswald and Fernand Noel . . 3948 Structure of an Aldotriouronic Acid Isolated from Jute Fiber Hemicellulose. H. C. Srivastava, C. T. Bishop, and G. A. Adams . . . . . 3958 Preparation, Physical Properties, and Configuration of the Isomers in PHOSDRINB Insecticide. Alan R. Stiles, Charles A. Reilly, Glenn R. Pollard, Charles H . Tieman, Loyal F. Ward, Jr., Donald D. Phillips, S. B. Soloway, and R. R. Whetstone . . . . . . . . . . . . . 3960 Organic Sulfur Compounds. V. Alkylammonium Thiolate and Peroxide Salts; Possible Intermediates in the Amine-Catalyzed Oxidation of Mercaptans by Hydroperoxides. Alexis A . Oswald, Fernand Noel, and Arthur J. Stephenson . . . . . . . . . . . . . . . 3969 Organic Sulfur Compounds. V. The Effect of Alkylamines on the Course of the Co-oxidation of Mercaptans and Indene. Alexis A. Oswald, Fernand Noel, and George Fisk . . . . 3974 The Preparation of Dithiooxamide Derivatives. Richard N . Hurd, George De La Mater, George C. McElheny, Robert J. Turner, and Vernon H. Wallingford . . . . . . . . . . . . . . . 3980 Carbonyl and Thiocarbonyl Compounds. V. Synthesis of Unsaturated Nitriles, Carboxylic

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Tables of Contents of ACS PUBLICATIONS Acids, and Esters Derived from Xanthene and Thiaxanthene. M . M . Hafez, N . Latif, and I . F. Zeid . . . . . . . . . . . . . . . . . Synthesis of a Series of Organophosphorus Esters Containing Alkylating Groups. Allen M . Gold . . . . . . . . . . . . . . . . . . The Condensation of Phosphonic Dichlorides with o-Diamines. Ralph L. Dannley and Philip L. Wagner . . . . . . . . . . . . . . The Reactions of 1,4-Bis(diphenyl-phosphino)benzene with Phenyl Azide and 1,4-Diazidobenzene. D. L . Herring . . . . . . . . . Studies in Organosilicon Chemistry. XXXIX. The Addition of Silanes to Isoprene. Isao Shiihara, Wesley F. Hoskyns, and Howard W . .Post . . . . . . . . . . . . . . . . . . Reactions of Perfluorosultones with Ammonia. H . H. Gibbsand M . I. Bra . . . . . . . . . a-Hydroperfluoroalkylaldehydes by Photoof a,a,@-Trihydroperfluorochlorination alkanols. Neal 0. Rrace . . . . . . . . . . Iminosulfur Oxydifluorides. Richard Cramer and D. D.Coffman . . . . . . . . . . . . . . Aromatic Fluorine Compounds. I. Preparation of p-Fluoroaniline by Catalytic Reduction of Nitrobenzene in Hydrogen Fluoride. Delmer A . Fidler, James S. Logan, and Max M . Boudakian . . . . . . . . . . . . . . . . Fluorinated C-Nitroso Compounds. 111. The Reaction of Nitrosyl Chloride with Some Fluoroolefins in the Presence of Ferric Chloride or Actinic Light. J. D. Park, A. P. Stefani, and J . R. Lacher. . . . . . . . . . . . . . Nucleophilic Substitution in Fluoroalkyl Sulfates, Sulfonates, and Related Compounds. Werner V . Cohen . . . . . . . . . . . . . Polymerization by the Diels-Alder Reaction. J . K . Stille and L . Plummer. . . . . . . . . Reaction Rates by Distillation. IX. The Condensation of Anilines with Benzaldehydes. Ernest F. Pratt and Mortimer J. Kamlet . . . . Oxine Ester Salicylates as Antifungal Agents. Nathaniel Grrer and Joseph A. Ramp , , , , . Ferrocenes. 111. Unsymmetrically Disubstituted Siloxanylferrocenes. Peter T . Kan, Carl T. Lenk, and Robert L. Schaaf, . . . . . Antihypertensive Agents: Derivatives of 2-Imidazoline and 1,4,5,6-Tetrahydropyrimidine. J . A . Faust, L . S. Yee, and M . Sahyun . . . . The Synthesis of Organic Trithiocarbonates. H . C. Godt, Jr., and R. E . W a n n . . . . . . . The Rearrangement and Cyclization of Ethyl N (Methylaminoalkyl)carbanilates and 1,lDimethyl 3 methylaminoalkyl - 3 - phenylureas. William B . Wright, Jr., and H . J. Brabander, . . . . . . . . . . . . . . . . . Debenzylation of Tertiary Benzylamines with Ethyl Chloroformate. William B . Wright, Jr., and Herbert J . Brabender . . . . . . . . The Stereospecific Synthesis of a Reserpine Analog. Paul B . LeVine and Ja.mes E. Gearien . . . . . . . . . . . . . . . . . CenJrally Active 2- (Substituted phenyl) a-alanmes. F. Leonard, A. Wajngurt, M . Klein, and C. M . Smith . . . . . . . . . . . . . Capillary Gas Chromatography of Phenyldodecane Alkylation and Isomerization Mixtures. R. .D. Swisher, E. F. Kaelble, and S . K. Liu . . Antiamebic Agents. V. Promising Basic Amebicides Derived from 5-Chloro-8-quinolinol. J. H. Burckhalter, William S. Brinigar, and Paul E . Thompson . . . . . . . . . . . . Amino- and Chloromethylation of 8-Quinolinol. Mechanism of Preponderant ortho Substitution in Phenols under Mannich Conditions. J . H . Burckhalter and Robert I . Lieb . . . . . . . .

3988 3991 3995 3998

Central Depressants. Phosphoramidates Dea-Disubstituted 4-Piperidinerived from CY, methanols. Frederick J . McCarty, Charles H . Tilford, and M . G. V a n Campen, Jr. . , . , . Synthesis and Antibacterial Activity of Some New Aminophosphinic Acids. W . M . Linfield, Eric Jungermann, and A. T. Guttmann. . The Dimerization of Vinyl- and Allylsilanes with Trialkylaluminums. William K . Johnson and Kenneth A. Pollart . , . . , . , . . Central Stimulants. 11. Cholinergic Blocking Agents. John H . Biel, Leo G. Abood, Wallace K . Hoya, Helen A . Leiser, Patrick A . Nuhfer, and E . F. Kluchesky. . . . . . . . . . . . ,

4084 4088 4092

4096

Notes 4000 4002 4005 4010

4014

4017 4021 4026 4029 4032 4038 4044 4047

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4051 4057 4060 4062 4066

4070

4078

Sulfonamides and Some Related Materials. H . Leighton Morrill, George W . Steahly, and Ferdinand B. Zienty. . . . . . . . . . . . 4103 2-Oxygenated 1,4,5,6,7,7-Hexachloro-5-norbornenes. William K . Johnson and Victor Mark 4105 Steroids. VII. Synthesis of Some 4-Azaandrostanes. Norman J. Doorenbos and Chien L i Huang . . . . . . . . . . . . . . . . . 4106 The Vapor Phase Pyrolysis of Several Substituted Azidobenzenes. Gerald Smolinsky , . 4108 2-Mercapto-2-phenylethylamine.Walter C. McCarthy and Beng-Thong Ho . . . . . . . . . 4110 Alkylation Reactions in Dimethyl Sulfoxide. Jordan J . Bloomfield. . . . . . . . . . . . 4112 Formation of Some Organometallic Compounds in Phenyl Ether. Henry Gilman and Gerald L. Schwebke . . . . . . . . . . . . . . . 4115 Derivatives of Some Nitroalkanes. Meldrum B . Winstead, Robert G. Strachan, and Harold W .Heine . . . . . . . . . . . . . . . . 4116 The Stereochemistry of Protonation of Anions of 9,lO Dihydro - 9,lO - (trans - 11-nitro - 12R-ethano)anthracenes. Wayland E. Noland and James M . Eakman. . . . . . . . . . . 4118 The Competitive Nitration of Toluene and t-Butylbenzene. Leon M . Stock. . . . . . . 4120 Cyanamide Derivatives. LIX. Preparation and Polymerization of Alkylenedicyanamide. Kiichiro Sugino, Kozo Shirai, and Rokuro Kitawaki . . . . . . . . . . . . . . . . . . 4122 Condensation Products of Glycine &Alkyl Esters. Arnulf Vollmar and Max S. Dunn . , . 4123 Preparation of Aromatic Nitramines. Alkaline Nitration Using Phenyllithium as Base. William N. White, Eugene F. Wolfarth, Joel R . Klink, James Kindig, Chester Hathaway, and DagnLja Lazdins . . . . . . . . . . . . . 4124 Reactions with Diazoalkanes. I. Action of Diazomethane on N-Phenylmaleimide, with a Special Note on the Pyrolysis Products of the Pyrazoline. William Ibrahim Awad, Sayed Mohamed Abdel, Rahman Omran, and Michael Sobhy . . . . . . . . . . . . . . . . . . 4126 MicrobiologicalTransformation of Steroids. IX. The Transformation of Reichstein’s Compound S by Scenedesmus sp. Diketopiperazine Metabolites from Scenedesmus sp. George Luedemann, William Charney, Americo Woyciesjes, Elliv Pettersen, William D . Peckham, Margaret Jevnik Gentles, Helen Marshall, and Hershel L . Herzog . . . . . . . . . . . . . 4128 Phenoxazines. 111. Dialkylaminoalkylphenoxazine-10 Carboxylates. M . Claesen and H . Vanderhaeghe . . . . . . . . . . . . . . 4130 Reaction of Chlorinated Urea Products with Ammonia and Ethylamine. Cornelius S. Groue, Jr., Gerald F . Grillot, and Richard C . Chang . . 4131 The Dialkylation of Cyanoacetic Ester with Chloromethyl-methylethoxysilanes. Omar W. Steward and Leo H . Sommer . . . . . . . 4132 The Reaction Product of Hydroxypivalaldehyde and Ammonia. Robert H . Hasek and James C. Martin . . . . . . . . . . . . . . . . . 4134 Synthesis of 1-Methyl-1-azaspiro[5.5 lundecan&one. Edgar Schipper and Edwin Chinery . . 4135

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NO. 12

DECEMBER 1961

107A

Tables of Contents of ACS PUBLICATIONS Synthesis of 3,3’-Thiobis(6-methylphenol). Frank J . Kreysa, Thomas R . Steadman, and Alio J. Buselli . . . . . . . . . . . . . . 4137 Homopiperazine and Its Derivatives. 11. A Convenient Synthesis of 1-Methylhomopiperazme. F. Poppelsdorf, R. C. Myerly, and R. B . Conrow . . . . . . . . . . . . . . . . . 4138 Preparation and Properties of 2-Hydroperfluoroalkyl Fluosulfonates. H . H . Gibbs, W . L . Edens, and R . N . Griffin . . . . . . . . . . 4140 Evidence for 9-Methylene-10-acetoxy-10-methyl9,lO-dihydrophenanthreneas an Intermediate. WilliamE. Adcock . . . . . . . . . . . . 4141 The Alkaloids of Liriodendron tulipifera L. The Structure and Synthesis of the Unnamed Yellow Alkaloid and the Isolation of d-Glaucine. J. Cohen, W. V o n Langenthal, and W. I . Taylor 4143 Some Properties and Reactions of Phenylacetoxysilanes. Yasuaki Nakaido and Toshio Takiguchi . . . . . . . . . . . . . . . . 4144 Derivatives of 2-Amino-1,3-propanediol.Edgar Schzpper, Edwin Chinery, and Joseph Nichols , 4145 Chloroethylation of Sulfuric Acid. G. E. Ham . 4148 The Camphenilanic and Camphenanic Acids. Joseph Wolbnsky . . . . . . . . . . . . . 4150 A Convenient Laboratory Preparation of p-Diacetylbenzene. J . R. Holsten and E. H . Pitts, J r . . . . . . . . . . . . . . . . . . . . 4151 Ethyl 2-S-Ethyl-1,2-dithio-5-aldehydo-~~-xylo (lyxo) pentodialdofuranoside. M . L . Wolfrom, Walter V o n Bebenburg, and A. Thompson . . . . . . . . . . . . . . . . . 4151 The Synthesis of 21-0-AlkylhydrocortisoneDerivatives and of llp-Hydroxy-17a,21-methylenedioxy-4-pregnene-3,2O-dione. William S. Allen and Martin J . Weiss . . . . . . . . . 4153 4 Dibutylamino - 2 methylpyrimidine - 5 -carTheodore D. boxaldehyde Semicarbazone. Perrine . . . . . . . . . . . . . . . . . 4155 A Convenient Method for the Preparation of Di-n-butylfluoroborane. E. J . DeWitt . . . 4156 Synthesis of Cyanotriphenylmethane from Hexaphenylethane. C. W . Schimelpfenig . . . . 4156 Reaction of 2-Aminopyridine with Propiolic Acid. Irwin J . Pachter . . . . . . . . . . 4157 Direct Synthesis of p-Styryldiphenylphosphine. RobertRabinowitzandRuth Marcus . . . . . 4157 The Thermal Decarboxylation of Diary1 Fumaratestostilbenes. Sydney M.Spatz . . . . 4158 Condensation and Addition Reactions of 3-Phenylindene. Borcs Weinstein . . . . . 4161 Oxidation of p-Nitrotoluene to 4,4’-Dinitrobibenzyl and 4,4’-Dinitrostilbene. Harry A . Stansbury, Jr., and William R. Proops . , . , 4162 New Syntheses of Aryl Fluorides and Aryl Fluorosulfonates from Oxyfluorides of Sulfur. Richard Cramer and D. D. Coffman . . . . . 4164 The Preparation of Some Arylalkenes. Edgar W . Garbisch, Jr. . . . . . . . . . . . . . 4165 The Synthesis of cis- and trans-1,4-Bis(2-aminoethy1)cyclohexanes. Paulina P. Garcia and Jesse Hermon Wood . . . . . . . . . . . 4167 Identification of a New, Naturally Occurring, Steam-Volatile Isothiocyanate from LesquereLla lasiocarpa Seed. Melvin E. Daxenbichler, C. H . V a n Etten, and Ivan A . Wolff . . . . . 4168 The Transformation of Squill Bufadienolides to Pyridone Counterparts. Frederick C. Uhle and Herbert Schroter . . . . . . . . . . . 4169 Preparation of Trimethylsilyl-Substituted Dihydric Phenols and Trimethylsilylbenzoquinone. Glenn D. Cooper, Barry Williams, and Cynthia P. Lape . . . . . . . . . . . . . . . . . 4171 Derivatives of l-Thia-4,5-diazacyclohepta-2,4,6triene. IV. Systems Containing Chloro Substituents. H . Harry Szmant and Rafael Infante . . . . . . . . . . . . . . . . . . 4173

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INDUSTRIAL AND ENGINEERING CHEMISTRY

Tetrahydroisoquinolinediones. I. The Structure of 4-Hydroxyisocarbostyril. Lyman R . Caswell and Richard D. Campbell . . . . . . 4175 Potential Cytostatic Carbohydrate Derivatives. I. N-Mustard Urethans. Thomas F. Nogrady . . . . . . . . . . . . . . . . . 4177

Communications a-Haloferrocenes. The Synthesis of Ferrocenylacetylene. Robert A. Benkeser and Walter P. Fitzgerald, Jr. . . . . . . . . . . . . . . Alkoxylation of Steroids with Cupric Bromide. Alcohol. Paul B . Sollman and R . M . Dodson . Microbiological Hydroxylation of Steroidal Alkaloids. Y . Sato and S. Hayakawa . . . . . . . A New Reaction for Forming Carbon-Phosphorus Bonds. Eric Jungermann and Joseph J . McBride, Jr.. . . . . . . . . . . . . . Halogenation of Unsaturated Aldehydes with Cupric Halides. C. E . Castro . . . . . . . B-Pyridylacrylophenones. A New Class of Active Coronary Dilating Agents. John Koo . . , , Photoisomerization of 3,5-Cycloheptadienones. 0. L. Chapman and G. W . Borden . . . . . .

4179 4180 4181 4182 4183 4185 4185

Journal of

CHEMICAL EDUCATION November 1961, Vol. 38, No. 11 Elements of Order-Disorder Theory: Applications to Gas Adsorption, Binary Solutions, Alloys, and Ferromagnetism. J . M . Honig . . . . . A Simple Method for Cleaning Buret Tips. William Michels. . . . . . . . . . . . . . A Redefinition of “Mole.” Shiu Lee , . , . , The Mole in Quantitative chemistry. George Nouello Copley . . . . . . . . . . . . . . Moles and Equivalents: Quantities of Matter. Irwin Cohen . . . . . . . . . . . . . . . Molecular Weights by Cryoscopy: A General Chemistry Laboratory Experiment. Robert Mikulak and Olaf Runquist . . . . . . . . . Analysis of an Aluminum-Zinc Alloy: A Quantitative Experiment for General Chemistry. William L. Masterton . . . . . . . . . . . An Easily Prepared Wide Range Buffer Series. Walter R. Carmody . . . . . . . . . . . . Robert Maskell Patterson; First to Teach Atomic Theory in America? Wyndham D . Miles . . . . . . . . . . . . . . . . . . Viscosities of Butanol-Heptane Mixtures: A Physical Chemistry Experiment. K . Keith Innes . . . . . . . . . . . . . . . . . . A Controlled Atmosphere Thermobalance. Wesley W. Wendlandt . . . . . . . . . . . A Thermobalance for Student Experiments. Rudolph S. Bottei and Paul L. Gerace . . . . A Simple Method for Finding Slopes. James P . Hoare . . . . . . . . . . . . . . . . . . Reaction Kinetics by Differential Thermal Analysis: A Physical Chemistry Experiment. Wesley W . Wendlandt . . . . . . . . . . . Nomographs for First and Second Order Kinetics. S. G. Smith and I . D. R. Stevens . . . . . . Ratio Errors in Pseudo First Order Reactions. Fred Sicilio and M . D. Peterson . . . . . . . A Teflon Bearing for Stirrers. M . L. Kaplan, R . E . Crocker, and Herbert Sargent . . . . . Float Method for the Analysis of Solutions. James 0. Osburn and II C . Choi . . . . . . Paper-made Crystal Models. Yasuyuki Komuro and K&‘3 Sone . . . . . . . . . . . . . . Proceedings of the California Association of Chemistry Teachers: Nuclear Magnetic Resonance Spectroscopy. John D. Roberts . . .

538 548 549 551 555 557 558 559 561 564 566 568 570 571 574 576 577 578 580 581