The deprotonation of 2-methyl-4,5,6,7-tetrahydro-3H-azepine (5) using lithium diisopropylamide was effected at −30°C in tetrahydrofuran. Addition of deuterium oxide resulted in >95% incorporation of deuterium at the exocyclic position. Addition of a range of electrophiles to the organolithium species afforded moderate yields of the alkylation products wherein substitution at the exocyclic position had occurred.
