N-bridged heterocycles. Part I. Synthesis and chemistry of NN′-polymethylene-o-phenylenediamines

Abstract

Methods have been eleborated for the synthesis of the series of NN′-polymethylene-o-phenylenediamines with 5–10 and 12 methylene groups. The interaction of these compounds with formaldehyde, benzaldehyde, and other aldehydes (to give bridged 2,3-dihydro-1H-benzimidazoles), with di-acid chlorides such as phosgene, thiophosgene, and oxalyl, succinyl, and sebacoyl chloride (to give various bridged heterocycles), with heterocumulenes such as carbon disulphide, and phenyl isocyanate and isothiocyanate, and with oxidising agents are reported.