A Schmidt route to 1-azabicyclo[x.y.0]alkanes: a comparison of carbocation stabilizing groups

被引:19
作者
Pearson, WH [1 ]
Walavalkar, R [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
基金
美国国家卫生研究院;
关键词
Schmidt reaction; carbocation; azide; aminodiazonium ion; indolizidine; quinolizidine;
D O I
10.1016/S0040-4020(01)00353-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular Schmidt reactions of tertiary alkyl, tertiary benzylic, tertiary propargylic, and tertiary allylic carbocations with tethered azides are reported. Using product analysis and deuterium labeling studies, the role of cation rearrangement prior to Schmidt reaction is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5081 / 5089
页数:9
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