Influence des groupestert-butyle, triméthylsilyle et triméthylgermyle sur la stéréochimie de réactions d'addition en série cyclohexénique. III. Epoxydation de cyclohexènes substitués en position allylique et réduction des époxydes par LiAlH4
作者:
Jean-Claude Richer,
Marc-André Poirier,
Yvette Maroni,
Georges Manuel,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1980)
卷期:
Volume 58,
issue 1
页码: 39-44
ISSN:0008-4042
年代: 1980
DOI:10.1139/v80-006
出版商: NRC Research Press
数据来源: NRC
摘要:
The epoxidation of allylic alkenes in the 6-tert-bulyl (or 6-trimethylsilyl or 6-trimethylgermyl) 3,3-dimethylcyclohexenes is examined; it has been found that the stereochemistry of these reactions is governed mostly by steric factors. The results obtained by the reduction ofcisandtransepoxides by lithium aluminium hydride are also reported, the regiochemistry and the stereochemistry of the reactions of reduction are governed by steric factors as well as by the electronic effects of the trimethylsilyl group.
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