THE CLEAVAGE OF PHOSPHORUS TO NITROGEN BONDS WITH HYDROGEN FLUORIDE

Abstract

Dialkyl phosphoramidates and alkyl P–alkylphosphonamidates react with hydrogen fluoride breaking the P—N bond to yield the corresponding fluoridates. This cleavage occurred when the nitrogen was unsubstituted, but the yield of product was increased by methyl substitution on the nitrogen. The reaction with diphenyl N,N-dimethylphosphoramidate was not restricted to the P—N bond, since cleavage of the CO—P bonds took place giving, as the ultimate product, hexafluorophosphoric acid. The results obtained indicate that hydrogen fluoride is the most efficient of the hydrogen halides in cleaving P—N bonds.