Aminimides. I. A general synthesis of aminimides from acyl hydrazides and their pyrolysis

Abstract

Acyclic, alicyclic, and aromatic bis-trimethylaminimides and a keto-substituted trimethylaminimide have been synthesized by a stepwise route of general applicability. Pyrolysis of the aliphatic aminimides resulted in a rearrangement to trimethylamine and isocyanate. The keto-isocyanate herein reported was synthesized in a convenient four-step sequence from dimethyl ketene dimer in a good yield, and provides an attractive new route to this type of difunctional compound. Pyrolysis of the bis-aminimides in the presence of polyhydroxylic materials gave polyurethanes.