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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