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.

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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 [J].

ALLEN, JV ;

COOTE, SJ ;

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

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 [J].

BENTLEY, RL ;

SUSCHITZKY, H .

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 [J].

BEUGELMANS, R ;

BOISCHOUSSY, M ;

BOUDET, B .

TETRAHEDRON, 1983, 39 (24) :4153-4161

[4] IMINYL RADICALS IN GAS-PHASE SYNTHESIS .1. GENERATION OF NITRILES BY PYROLYSIS OF ARYL AZINES [J].

BIRD, KJ ;

CHAN, AWK ;

CROW, WD .

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 [J].

Black, M ;

Cadogan, JIG ;

Leardini, R ;

McNab, H ;

McDougald, G ;

Nanni, D ;

Reed, D ;

Zompatori, A .

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 [J].

BUCHWALD, SL ;

WATSON, BT ;

LUM, RT ;

NUGENT, WA .

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 [J].

CADOGAN, JIG ;

HUTCHISON, HS ;

MCNAB, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :385-393

[8] SHORT CONTACT TIME REACTIONS OF LARGE ORGANIC FREE-RADICALS [J].

CADOGAN, JIG ;

HICKSON, CL ;

MCNAB, H .

TETRAHEDRON, 1986, 42 (08) :2135-2165

[9] GAS-PHASE GENERATION AND CYCLIZATION REACTIONS OF SOME ORTHOSUBSTITUTED PHENYL RADICALS [J].

CADOGAN, JIG ;

HUTCHISON, HS ;

MCNAB, H .

TETRAHEDRON, 1992, 48 (36) :7747-7762

[10]

CADOGAN JIG, 1987, THESIS U EDINBURGH