Synthesis, structures, and properties of new sterically hindered hydrazine-based catecholaldimines

Abstract

New sterically hindered catecholaldimines derived from hydrazine were synthesized in high yields. Two procedures for the synthesis of sterically hindered catecholaldimines were developed: by the reaction of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde with hydrazines (hydrazine hydrate, phenyl-, 1,1-diphenyl-, and (diphenylmethylene)hydrazines, acetyl and benzoyl hydrazides) or by the reaction of 3,5-di-tert-butyl-6-(hydrazonomethyl)catechol with a carbonyl compound (the reaction with 4-N,N-dimethylaminobenzaldehyde). The X-ray diffraction analysis and IR, UV, and NMR spectroscopic studies showed that these compounds exist in the catecholic form both in solution and the crystalline state.