Aliphatic hydroxylamines. Part IV. N-hydroxyhexamethyleneimine

Abstract

N-Hydroxyhexamethyleneimine contrasts with the lower six-membered ring homologue in that it has some of the properties of a drying oil. The cyclic nitrone, which appears to be an intermediate in the autoxidation, has been prepared independently by hydrogen transfer using benzoquinone as hydrogen acceptor; it polymerises rapidly. A dimer is formed in small amount during the autoxidation of N-hydroxyhexamethyleneimine and has been shown to be a 14-membered ring dinitrone. An hypothesis, which rationalises these and other observations, is presented.