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

页码：1079 / 1085

页数：7

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