Synthesis and X-ray crystal structures of 1-(NN-dimethylaminomethylidene)-3-phenylisoindolenine and 1-formyl-3-phenylisoindole

Abstract

1-Phenylisoindole reacts with the Vilsmeier reagent to give 1-(NN-dimethylaminomethylidene)-3-phenylisoindole (4), which on basic hydrolysis furnishes 1-formyl-3-phenylisoindole (5). X-Ray structure analyses have been carried out on (4) and (5). The latter structure is the first available for an isoindole with a simple substitution pattern, and provides information bearing on the aromaticity of the isoindole nucleus.