REACTIVITY OF N-ALKYL DERIVATIVES OF HYDROXYLAMINE IN DECOMPOSITION OF 4-NITROPHENYL DIETHYLPHOSPHONATE IN WATER AND IN CETYLTRIMETHYLAMMONIUM BROMIDE MICELLES

Neutral forms of hydroxylamine, N-methylhydroxylamine, and N,N-dimethylhydroxylamine are typical alpha-nucleophiles in water. In comparison with aryl anions of similar basicity their rate of reaction in the decomposition of 4-nitrophenyl diethylphosphonate is increased by about 102 times. Decomposition of the substrate is accelerated in cetyltrimethylammonium bromide micelles (about 4 to 30 fold). Hydroxylamine and its N-alkyl derivatives are the most effective low basicity nucleophiles. The sole factor responsible for the micellar effects is the concentration of the reagent in the surfactant micelles.