Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates

被引:24
作者
Calestani, G
Leardini, R
McNab, H
Nanni, D
Zanardi, G
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
[2] Univ Parma, Dipartimento Chim Gen & Inorgan Analit & Chim Fis, I-43100 Parma, Italy
[3] CNR, Ctr Studio Strutturist Diffrattometr, I-43100 Parma, Italy
[4] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 11期
关键词
D O I
10.1039/a800868j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process, Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant-in some cases major-amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.
引用
收藏
页码:1813 / 1824
页数:12
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