Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

被引:27
作者
Creed, T
Leardini, R
McNab, H
Nanni, D
Nicolson, IS
Reed, D
机构
[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 09期
关键词
D O I
10.1039/b009844m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Flash vacuum pyrolysis (FVP) of the oxime ethers 12-14 and of the sulfides 18-20 at 650 degreesC (10(-2)-10(-3) Torr) gave products derived from the corresponding iminyl and thiophenoxyl radicals. In all cases, benz[d]isothiazoles (e.g., 26) are formed as major products via S(H)i mechanisms though the yields are greatest with the iminyl precursors. Alternative pathways observed from the thiophenoxyls in specific cases include the formation of the anilinobenzothiophene 36 and of dibenzothiophene 23, via an S(H)i process and a spirodienyl rearrangement, respectively. There is no evidence for significant interconversion of the iminyl and thiophenoxyl species.
引用
收藏
页码:1079 / 1085
页数:7
相关论文
共 29 条
  • [1] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS
    ALLEN, JV
    COOTE, SJ
    DAWSON, GJ
    FROST, CG
    MARTIN, CJ
    WILLIAMS, JMJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2065 - 2072
  • [2] SYNTHESES OF HETEROCYCLIC-COMPOUNDS .33. PREPARATION AND REACTIONS OF 4-(2-DIALKYLAMINOPHENYL)AZETIDIN-2-ONES
    BENTLEY, RL
    SUSCHITZKY, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (16): : 1725 - 1734
  • [3] STUDY OF SRN1 REACTIONS .10. ACTION OF SULFANIONS ON FUNCTIONALIZED ARYL HALIDES - DIRECT SYNTHESIS OF BENZOTHIOPHENES AND THIENOPYRIDINES
    BEUGELMANS, R
    BOISCHOUSSY, M
    BOUDET, B
    [J]. TETRAHEDRON, 1983, 39 (24) : 4153 - 4161
  • [4] IMINYL RADICALS IN GAS-PHASE SYNTHESIS .1. GENERATION OF NITRILES BY PYROLYSIS OF ARYL AZINES
    BIRD, KJ
    CHAN, AWK
    CROW, WD
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (10) : 2281 - 2287
  • [5] A study of the gas-phase interconversion of 1-(2-aryloxyphenyl)alkaniminyl and 2-(aryliminomethyl)phenoxyl radicals
    Black, M
    Cadogan, JIG
    Leardini, R
    McNab, H
    McDougald, G
    Nanni, D
    Reed, D
    Zompatori, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (11): : 1825 - 1832
  • [6] A GENERAL-METHOD FOR THE PREPARATION OF ZIRCONOCENE COMPLEXES OF SUBSTITUTED BENZYNES - INSITU GENERATION, COUPLING REACTIONS, AND USE IN THE SYNTHESIS OF POLYFUNCTIONALIZED AROMATIC-COMPOUNDS
    BUCHWALD, SL
    WATSON, BT
    LUM, RT
    NUGENT, WA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) : 7137 - 7141
  • [7] GAS-PHASE REACTIONS OF 2-BENZYL RADICAL AND 2-BENZOYL-PHENOXYL RADICAL, AND OF 2-PHENOXYBENZYL RADICALS - EXAMPLES OF NEW HYDROGEN-TRANSFER PROCESSES
    CADOGAN, JIG
    HUTCHISON, HS
    MCNAB, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 385 - 393
  • [8] SHORT CONTACT TIME REACTIONS OF LARGE ORGANIC FREE-RADICALS
    CADOGAN, JIG
    HICKSON, CL
    MCNAB, H
    [J]. TETRAHEDRON, 1986, 42 (08) : 2135 - 2165
  • [9] GAS-PHASE GENERATION AND CYCLIZATION REACTIONS OF SOME ORTHOSUBSTITUTED PHENYL RADICALS
    CADOGAN, JIG
    HUTCHISON, HS
    MCNAB, H
    [J]. TETRAHEDRON, 1992, 48 (36) : 7747 - 7762
  • [10] CADOGAN JIG, 1987, THESIS U EDINBURGH