Cyclic meso-ionic compounds. Part VI. Synthesis, spectroscopic properties, and dipole moments of the isosydnones

Abstract

The isosydnones, obtained by the reaction of N-acyl-N-(alkyl or aryl)hydrazine hydrochlorides with carbonyl chloride, have u.v., i.r., and n.m.r. spectral characteristics supporting their formulation as meso-ionic compounds. A number of suitably substituted isosydnones have been prepared and measurement of their dipole moments establishes the direction and magnitude of the heterocyclic ring moment which is in accord with the meso-ionic structure of the isosydnones.