Influence des groupes tert-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 | Zendy

JeanClaude Richer | Zendy; M A Poirier | Zendy; Yvette Maroni | Zendy; Georges Manuel | Zendy

Open Access

Influence des groupes tert-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

Author(s) -

JeanClaude Richer,

M A Poirier,

Yvette Maroni,

Georges Manuel

Publication year - 1980

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v80-006

Subject(s) - chemistry , steric effects , allylic rearrangement , trimethylsilyl , medicinal chemistry , regioselectivity , lithium aluminium hydride , stereochemistry , lithium (medication) , catalysis , organic chemistry , medicine , endocrinology

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 of cis and trans epoxides 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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