Protonated cyclopropanes in α-aminoketone deamination
作者:
Oliver E. Edwards,
John Dixon,
John W. Elder,
Ralph J. Kolt,
Maurice Lesage,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1981)
卷期:
Volume 59,
issue 14
页码: 2096-2115
ISSN:0008-4042
年代: 1981
DOI:10.1139/v81-305
出版商: NRC Research Press
数据来源: NRC
摘要:
Deamination of 2-amino-4,4-dideuterio-6,6-dimethylcyclohexanone, 2-exo-amino- and 2-endo-amino-norbornane-3-one, 2-diazo-norbornan-3-one, 2-exo-amino-5,6-exo-dideuterionorbornan-3-one and the corresponding 5,6-endo-dideuterio isomer has been studied. The nature of the products, the deuterium location in them, and the high retention of steric identity in the carbocations are interpreted in terms of σ-bond participation leading to corner- and edge-protonated cyclopropanes as reaction intermediates. Results with other destabilized carbocations are correlated.
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