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REDUCTION OF CONJUGATED CYCLOHEXENONE OXIMES WITH ALUMINIUM HYDRIDE
Zaidlewicz, Marek,Uzarewicz, Ireneusz G.
, p. 143 - 150 (2007/10/02)
The reduction of representative conjugated cyclohexenone oximes with aluminium hydride in tetrahydrofuran yields 2-cyclohexenylamines and saturated aziridines - 7-azabicycloheptane derivatives, as the main reaction products.Small quantities of cyclohexylamines and perhydroazepines are also formed.Regioselectivity of the reduction depends on oxime configuration.Higher yields of 2-cyclohexenylamines are obtained from E than Z isomers.The reaction mechanism is proposed.
