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The Journal of Organic Chemistry 1975 Volume 40 No.19 V O LLM E 40 SEPTEMBER 19, 1975 NUM BER 19 J OC EAh 'ü a ío b s PUBLISHED BIWEEKLY BY THE AMERICAN CHEMICAL SOCIETY t h e j o u r n a l o f Organic Chem istry EDITOR-IN-CHIEF: FREDERICK D. GREENE Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 SENIOR EDITORS Werner Herz James A. Moore Martin A. Schwartz Florida State University University of Delaware Florida State University Tallahassee, Florida Newark, Delaware Tallahassee, Florida ASSISTANT EDITOR: Theodora W. Greene ADVISORY BOARD Robert A. Benkeser Robert J. Highet James C. Martin Henry Rapoport John I. Brauman Ralph Hirschmann Albert I. Meyers Robert V. Stevens Clifford A. Bunton William M. Jones John G. Moffatt Edward C. Taylor Orville L. Chapman Jay K. Kochi Roy A . Olofson Barry M. Trost Stanton Ehrenson Walter Lwowski Leo A. Paquette Nicholas J. Turro David A. Evans James A. Marshall Marvin L. Poutsma EX-OFFICIO MEMBERS: George H. Coleman, Sanibeiisland, Florida Edward M . Burgess, Georgia Institute of Technology (Secretary-Treasurer of the Division of Organic Chemistry of the American Chemical Society) Published by the Editorial Processing Department, Amer­ On changes of address, include both old AMERICAN CHEMICAL SOCIETY ican Chemical Society, 20th and North­ and new addresses with ZIP code num­ 1155 16th Street, N. W. ampton Sts., Easton, Pa. 18042: Depart­ bers, accompanied by mailing label from a Washington, D C. 20036 ment Head, Charles R. Bertsch; Associate recent issue. Allow four weeks for change Department Head, Marianne C. Brogan; to become effective. Production Editor, Eileen B. Segal; Assis­ Claims for missing numbers will not be BOOKS AND JOURNALS DIVISION tant Editor, Fern S. Jackson; Editorial allowed (1 ) if loss was due to failure of no­ Assistant, Andrew J. D’Amelio; Production tice of change in address to be received be­ Assistant, Jane U. Lutick. fore the date specified, (2 ) if received more D. H. Michael Bowen Director Advertising Office: Centcom, Ltd., 50 than sixty days from date of issue plus W. State St., Westport, Conn. 06880. time normally required for postal delivery The American Chemical Society and the of journal and claim, or (3) if the reason Editors of The Journal of Organic Chemis­ for the claim is “ issue missing from files.” try assume no responsibility for the state­ Subscription rates (hard copy or micro­ Charles R. Bertsch Head, ments and opinions advanced by contribu­ Editorial Processing Department fiche) in 1975: $20.00 to ACS members, tors. $80.00 to nonmembers. Extra postage $6.00 Business and Subscription Information in Canada and PUAS, $6.50 other foreign. Bacii Guiley Head, Graphics and Supplementary material (on microfiche Send all new and renewal subscriptions Production Department only) available on subscription basis, 1975 to Office of the Controller, with payment rates: $15.00 in U.S., $19.00 in Canada and 1155 16th Street, N.W., Washington, D.C. PUAS, $20.00 elsewhere. All microfiche 20036. Subscriptions should be renewed Seldon W. Terrant Head, Research airmailed to non-U.S. addresses; air freight and Development Department promptly to avoid a break in your series. All correspondence and telephone calls re­ rates for hard-copy subscriptions available garding changes of address, claims for on request. missing issues, subscription service, the Single copies for current year: $4.00. status of records, and accounts should be Rates for back issues from Volume 20 to © Copyright, 1975, by the American directed to Manager, Membership and date are available from the Special Issues Chemical Society. 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Notice to Authors last printed in the issue of June 27, 1975 JOCEAh (19) 2697-2852 (1975) ISSN 0011-3263 THE JOURNAL OF Organic Chemistry V o l u m e 40, N u m b e r 19 Se p t e m b e r 19,1975 Ryoichi Katakai 2697 Peptide Synthesis Using o-Nitrophenylsulfenyl V-Carboxy «-Amino Acid Anhydrides Yasumitsu Tamura,* 2702 Photochemical Syntheses of 2-Aza- and 2-Oxabicyclo[2.1.1]hexane Hiroyuki Ishibashi, Michio Hirai, Ring Systems Yasuyuki Kita, and Masazumi Ikeda Peter Y. Johnson,* Irwin Jacobs, 2710 The Chemistry of Hindered Systems. Syntheses and Properties of and Daniel J. Kerkman Tetramethylazacycloheptanes and Related Acyclic Amines Boris B. Gavrilenko and 2720 Synthesis and Properties of 3-Amino-3-pyrazolin-5-ones Sidney I. Miller* David A. Lightner* and 2724 Dye-Sensitized Photooxygenation of fert-Butylpyrroles Chwang-Siek Pak Friedrich W. Vierhapper and 2729 Selective Hydrogenation of Quinoline and Its Homologs, Isoquinoline, Ernest L. Eliel* and Phenyl-Substituted Pyridines in the Benzene Ring Friedrich W. Vierhapper and 2734 Reduction of 5,6,7,8-Tetrahydroquinolines and Ernest L. Eliel* 2,3,4,5,6,7,8,10-Octahydroquinolines to frans-Decahydroquinolines Richard Y. Wen, Andrew P. Komin, 2743 The Chemistry of 1,2,5-Thiadiazoles. II. 3,4-Disubstituted Derivatives Robert W. Street, and Marvin Carmack* of 1,2,5-Thiadiazole 1,1-Dioxide Andrew P. Komin, Robert W. Street, 2749 The Chemistry of 1,2,5-Thiadiazoles. III. and Marvin Carmack* [l,2,5]Thiadiazolo[3,4-c][l,2,5]thiadiazole Charles O. Okafor 2753 Studies in the Heterocyclic Series. X. 1,3,9-Triazaphenothiazine Ring System, a New Phenothiazine Ring Serugudi R. Mani and Henry J. Shine* 2756 Ion Radicals. XXXIV. Preparation of Phenoxathiin Cation Radical Perchlorate. Formation and Reactions of S-Iminophenoxathiin (Phenoxathiin Sulfilimine) Ashok K. Sharma, Thomas Ku, 2758 Dimethyl Sulfoxide-Trifluoroacetic Anhydride. A New and Efficient Arthur D. Dawson, and Daniel Swern* Reagent for the Preparation of Iminosulfuranes Thomas M. Santosusso and 2764 Acid-Catalyzed Reactions of Epoxides with Dimethyl Sulfoxide Daniel Swern* Eric Block,* Michael D. Bentley, 2770 Electron Impact Induced Processes of Thermally and Photochemically Franklin A. Davis, Irwin B. Douglass, ■ Labile Organic Sulfur Compounds. A Mass Spectral Study of Dialkyl and John A. Lacadie Thiolsulfonates, Disulfides, Trisulfides, and a-Disulfones Lamar Field* and 2774 Organic Disulfides and Related Substances. 39. Study of Insertion Catherine Hamrick Banks Reactions Using Carbenoids, Carbenes, Ylides, and Nitrenes Larry E. Overman* and 2779 Nucleophilic Cleavage of the Sulfur-Sulfur Bond by Phosphorus Stephen T. Petty Nucleophiles. III. Kinetic Study of the Reduction of a Series of Ethyl Aryl Disulfides with Triphenylphosphine and Water Shizen Sekiguchi* and Keiji Okada 2782 Aromatic Nucleophilic Substitution. V. Conformation of the Spiro Janovsky Complex in Base-Catalyzed Rearrangement of N-Acetyl-j8-aminoethyl-2,4-dinitrophenyl Ether with Simultaneous Migration of Acetyl Group Yoshinori Hara and Minoru Matsuda* 2786 Cleavage Reaction of Cyclic Ethers by Alkyl Chlorosulfinates C. A. Franz and Donald J. Burton* 2791 Fluoro Olefins. VI. Ring Size Effects in Cyclic Fluoro Olefins with Alkoxide Nucleophiles Donald J. Burton* and 2796 Fluoro Olefins. VII. Preparation of Terminal Vinyl Fluorides Peter E. Greenlimb W. Ronald Purdum and 2801 A Rapid Method of Preparation of Phospholanium Perchlorates via K. Darrell Berlin* Intramolecular Cyclizations of 4-Hydroxybutylorganophosphines John T. Groves* and 2806 Synthesis and Solvolysis of Tricyclo[4.3.2.02-5]undeca-3,8,10-trien-7-ol. Christian A. Bernhardt An Unusual [CH]n+ Rearrangement 2A J. Or g. Chem., Vol. 40, No. 19,1975 Attention Cas Chrom atographen Derlvatixing Agents The following are some of the derivatizing agents available from PCR stock. 2 7 0 9 0 Chloromethyldimethylchlorosilane (CMDMCS) 50g—$15.25; 250g—$60.00 3 4 0 4 0 N.N-Diethylammotrimethylsilane (Trimethyl-N.N-diethylaminosilane) 10g $20.00; 50g- $ 8 0 .0 0 1 3 0 9 0 Heptafluorobutyric acid 5 0 g —-$15.00; 250g- $ 6 2 .5 0 1 3 1 0 0 Heptafluorobutyric anhydride 2 5 g —-$19.50; 100g- $ 6 1 .0 0 1 3 1 2 0 Heptafluorobutyryl chloride 2 5 g - -$16.00; 100g- $ 6 0 .0 0 3 4 0 2 0 Hexamethyldisilazane (HMDS) 1 0 0 g --$12.00; 500g- $ 2 5 .0 0 3 4 0 9 0 1,1,3,3-T etramethy Idisilazane 25g -$21.00; 100g- $ 6 5 .0 0 1 1 0 2 3 Trifluoroacetic acid Polyethers (High Purity Fe Free) 1 0 0 g - $10.00; 500g- $ 4 0 .0 0 1 3 2 0 0 Trifluoroacetic anhydride 100g -$12.00; 1kg- $88.00 2 7 4 9 0 Trimethylchlorosilane (TMCS) ACS Symposium Series No. 6 100g—$10.00; 500g-$25.00 NOTE : Minimum order: $25.00 Edwin J. Vandenberg, E d ito r Thirteen papers from a sympo­ PI R, INCORPORATED sium sponsored by the Division Research Chemicals Division of Polymer Chemistry of the P.O. Box 1466/GainesviHe, Florida 32602 American Chemical Society. {904‘ 376 V522 A valuable sourcebook providing full coverage of the latest-polyether research with investigations fo c u s ­ ing on crystalline structures, reac­ Here is a comprehensive collection tion mechanisms, and kinetics. of current and early orbital sym­ metry literature providing the stu­ dent, teacher, and scientistwith one Discussions are largely concerned handy, complete
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