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Stereochemistry of the conventional and modified Bucherer–Bergs reactions of 2-substituted cyclohexanones

 

作者: Guerino Sacripante,   John T. Edward,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1982)
卷期: Volume 60, issue 15  

页码: 1982-1987

 

ISSN:0008-4042

 

年代: 1982

 

DOI:10.1139/v82-279

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The configurations of the spiro-hydantoins produced from 2-methyl- and 2-phenylcyclohexanone, 2,6-dimethylcyclohexanone, anddl-menthone by either the conventional Bucherer–Bergs (B•–B•) reaction, or a variant employing COS or CS2in place of CO2, have been established by13C nmr. In all cases the conventional B•–B•reaction gave the hydantoin having the 4′-carbonyl group equatorial, and the COS or CS2variant, the mono- or dithiohydantoin having the 4′-thiocarbonyl group, axial.

 

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