On the edge of the steric repulsion and reactivity of bulky anilines; a case study of chloro(imino)phosphine synthesis

Abstract

2-Benzhydryl-4-methyl-6-(1,1′-diphenyl-2-phenyl-ethyl)aniline was prepared by a three-step process. 2,6-Bis(benzhydryl)-4-methyl-aniline was protected by Schiff coupling, then benzylated and finally dealkylated by using hydrochloric acid and methanol. The resulting compound exhibits one of the highest buried volumes around the nitrogen atom of anilines prepared so far, but it reacts with phosphorus trichloride and triethylamine to give a monomeric chloro(imino)phosphine.