Deprotonation and alkylation of 2-methyl-4,5,6,7-tetrahydro-3H-azepine
The deprotonation of 2-methyl-4,5,6,7-tetrahydro-3H-azepine (5) using lithium diisopropylamide was effected at -30°G 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.
CYCLIC β-ENAMINOESTERS DECARBOXYLATION WITH BORIC ACID : A CONVENIENT SYNTHESIS OF CYCLIC IMINES
Δ1-pyrrolines, Δ1-piperideines and 1-aza 1-cycloheptenes are formed in good yields from the decarboxylation of alkylated cyclic β-enaminoesters with boric acid.