- Protonated cyclopropanes in α-aminoketone deamination
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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 ?-bond participation leading to corner- and edge-protonated cyclopropanes as reaction intermediates.Results with other destabilized carbocations are correlated.
- Edwards, Oliver E.,Dixon, John,Elder, John W.,Kolt, Ralph J.,Lesage, Maurice
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p. 2096 - 2115
(2007/10/02)
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