O-(diphenylphosphinyl)hydroxylamine: preparation and some characteristic chemical reactions

Abstract

Hydroxylamine reacts with diphenylphosphinic chloride (1) in benzene (or aqueous dioxan) to give O-(diphenylphosphinyl)hydroxylamine (3) and not the N-phosphinyl compound (2) as was previously thought. Di-p-tolyl-,bis-p-methoxphenyl-, and phenyl-p-methoxphenyl-phosphinic chlorides are similarly attacked by the oxygen of hydroxylamine. The structures of the phosphinylhydroxylamines can be inferred from their chemical reactions; in particular they condense with acetone to give phosphinylacetone oximes (8) identical to those obtained from phosphinic chlorides and acetone oxime. Like O- sulphonylhydroxylamines, O-(diphenylphosphinyl)hydroxyl-amine form aminophosphonium and aminosulphonium salts with triphenylphosphine and dimethyl sulphide respectively.