Reactions of Phosphonioalkyl Derivatives of Phenylhydrazine and Hydroxylamine

Abstract

Triphenyl- and tributyl[2-(2-phenylhydrazino)ethyl]phosphonium salts undergo dehydrogenation on heating to form the corresponding phenylhydrazones in high yields. The phenylhydrazone formed from the triphenylphosphonium salt can also be prepared from triphenyl(1-alkoxy-2-bromoethyl)phosphonium bromides. The latter reaction is proposed to involve reduction of the COC group with phenylhydrazine. N,N-Diphosphonioethylation and N,N-diphosphoniopropylation of hydroxylamine are performed. Alkaline hydrolysis of the resulting diphosphonium salts gave N, N-bis[2-(diphenylphosphoryl)ethyl(propyl)]hydroxylamines in high yields.