It has been known for some time that alkylations with tertiary amines of the type RCHzN- (CH3) z and their quaternary salts proceed much inore readily when R is 2-pyrryI2 (11) or 3- indoly13 (111) than when R is phenyl4 (I). The hypothesis that the enhanced reactivity of the heterocyclic amines is due to the operation of an elimination-addition mechanism5 is inadequate, since 1-methylgramine (IV) which cannot react by such a mechanism also ...