Thermal decomposition of tert-butyl ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)phenyliminoxyperacetates:: The reactivity of thio-substituted iminyl radicals

被引:32
作者
Leardini, R
McNab, H
Minozzi, M
Nanni, D
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
[2] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 09期
关键词
D O I
10.1039/b009843o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)-substituted phenyliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The sulfanyl-substituted iminyls showed no tendency to give either 1,7- or 1,6-ring closure onto the S-phenyl ring. They gave instead 1,5-cyclisation onto the sulfur atom with release of a phenyl radical and formation of benzoisothiazoles. This seems to be the first example of S(H)i reaction of a nitrogen-centred radical at a sulfide moiety. On the other hand, the sulfonyl-substituted iminyl underwent 1,6-cyclisation to a small extent, furnishing a phenanthridine through an unprecedented 1,5-aryl radical migration from sulfur to nitrogen followed by loss of sulfur dioxide and ring closure of an aryl radical.
引用
收藏
页码:1072 / 1078
页数:7
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