Synthesis of N,N-bis(3-butenyl)amines from 2-azaallyl dication synthetic equivalents and conversion to 2,3,6,7-tetrahydroazepines by ring-closing metathesis

The reactivity of (2-azaallyl)nitriles toward double nucleophilic addition and the double allylation reactions of (2-azaallyl)stannanes are reported. The conversion of the N,N-bis(3-butenyl)amines obtained as products from the double allylation reactions to 2,3,6,7-tetrahydroazepines through ring-closing metathesis is described.