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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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