ALKOXYNITRENIUM ION CYCLIZATIONS - EVIDENCE FOR DIFFERENT MECHANISMS IN THE FORMATION OF BENZOXAZINES AND BENZOXAZEPINES

被引：30

作者：

GLOVER, SA ^{[1
]}

ROWBOTTOM, CA ^{[1
]}

SCOTT, AP ^{[1
]}

SCHOONRAAD, JL ^{[1
]}

机构：

[1] UNIV PORT ELIZABETH,PORT ELIZABETH 6000,SOUTH AFRICA

来源：

TETRAHEDRON | 1990年 / 46卷 / 20期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/S0040-4020(01)87905-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deuterium labelling experiments and n.m.r.studies indicate that cyclisations of N-acyl-N-(2-phenylethyloxy) nitrenium ions occur via direct attack at the ortho position to give 34-dihydro-1 H-21-benzoxazines. In contrast N-acyl-N-(3-phenylpropyloxy)nitrenium ions cyclise to 1345-tetrahydro-21-benzoxazepines through ipso attack followed by 12-carbon migration. In both cases hydrogen circumambulation occurs in the sigma complex before aromatisation. © 1990.

引用

页码：7247 / 7262

页数：16

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