Amide as a protecting group in phosphate ester synthesis. Part II. A non-hydrolytic conversion of phosphoramidates into phosphates

The action of nitrosating agents on N-alkyl phosphoramidic diesters has been studied. The N-methyl compounds were converted in high yield into the corresponding phosphate diesters; only small amounts of triester were formed. Phosphoramidates with higher alkyl groups attached to nitrogen gave lower yields of diester. The mechanism of the reaction is discussed.