Abstract
Reduction of several 2-benzylidenecyclohexanone oximes with lithium aluminum hydride gave the corresponding 1-benzyl-1,2-epiminocyclohexanes. Reduction of 2-benzylidenecyclohexanone oxime with lithium aluminum deuteride gave an epiminocyclohexane (8) which had incorporated two deuterium atoms. A reaction mechanism for the reduction is postulated. The major fragmentation pathways in the mass spectrum of 8 are outlined. Acetylation of 1-benzyl-1,2-epiminocyclohexane with acetic anhydride (15 min reflux) gave 3-acetamido-2-benzyl-1-cyclohexene by a pyrolytic cis elimination.
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