Synthesis and structure of N-alkoxyhydrazines and N-alkoxy-N',N',N'-trialkylhydrazinium salts

Abstract

New types of 1,1,1-trialkyl-2-alkoxyhydrazinium chlorides and N-alkoxyhydrazines were obtained by reactions of N-chloro-N-alkoxyureas with trimethylamine or 1,4-diaza[2.2.2]bicyclooctane and by reactions of methyl N chloro-N-methoxycarbamate with potassium salt of N-acetylbenzenesulfonylamide. The XRD studies of N,N' bis(methoxycarbonyl)-N,N'-dimethoxyhydrazine, N'-methoxy-N'‑methoxycarbonyl-N-acetylbenzenesulfonylhydrazide and 1,1,1-trimethyl-2-methoxyhydrazinium perchlorate revealed the pyramidal configuration of the central nitrogen atoms in O–N–N geminal system, unusual elongation of N–N+ bond and shortening of N–OMe bond in 1,1,1-trimethyl-2-methoxyhydrazinium perchlorate.