Protonated cyclopropanes in α-aminoketone deamination

…, J Dixon, JW Elder, RJ Kolt, M Lesage

Index: Edwards, Oliver E.; Dixon, John; Elder, John W.; Kolt, Ralph J.; Lesage, Maurice Canadian Journal of Chemistry, 1981 , vol. 59, p. 2096 - 2115

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Citation Number: 7

Abstract

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 ...