The limited scope of azabicyclohexane synthesis from δ,ε-unsaturated amines

Abstract

The reported synthesis of 1-azabicyclo[3,1,0]hexanes from β,β-diphenyl δ,ε-unsaturated alkylamines has been verified and extended. However, similar treatment of alkyl-substituted δ,ε-unsaturated alkylamines with bromine and sodium hydride fails to afford azabicyclohexanes and unsaturated acyclic products are formed. It is concluded that satisfactory synthesis of azabicyclohexanes from δ,ε-unsaturated amines is contingent on the presence of suitable bulky substituents.