Abstract
The reaction of 2-(bromomethyl)benzonitrile (5) with hydrazides 6a-f or heterocyclic amines 14a-c gave isoindolium bromides 7a-f and 15a-f, respectively. Deprotonation of the latter salts afforded the 1,2-aza-ylides 8a-f and 1,3-aza-ylides 16a-c instead of the analogous imines 9a-f or 17a-c, respectively. Single crystal X-ray and NMR analyses confirmed the stable ylide structures of 8a-f and 16a-c and established the presence of a complete benzenoid unit in the isoindole moiety, in both the solid state and solution phase.