Synthesis of Some Epiminocyclohexanes by Hydride Reduction of α,β-Unsaturated Cyclohexanone Oximes and the Pyrolyticcis-Elimination ofN-Acetylepiminocyclohexanes
作者:
J. R. Dimmock,
W. A. Turner,
P. J. Smith,
R. G. Sutherland,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1973)
卷期:
Volume 51,
issue 3
页码: 427-432
ISSN:0008-4042
年代: 1973
DOI:10.1139/v73-063
出版商: NRC Research Press
数据来源: NRC
摘要:
Reduction of several 2-benzylidenecyclohexanone oximes with lithium aluminum hydride gave the corresponding 1-benzyl-1,2-epiminocyclohexanes. Reduction of 2-benzylidenecyclohexanone oxime with lithium aluminum deuteride gave an epiminocyclohexane (8) which had incorporated two deuterium atoms. A reaction mechanism for the reduction is postulated. The major fragmentation pathways in the mass spectrum of8are outlined. Acetylation of 1-benzyl-1,2-epiminocyclohexane with acetic anhydride (15 min reflux) gave 3-acetamido-2-benzyl-1-cyclohexene by a pyrolyticciselimination.
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