Hydroxamates dephosphorylation

NC6H40)2P0.0Et + hydroxamates Dephosphorylations by mixed micelles, vesicles and hydrophobic hydroxamic acid compared Okahata et al., 1981... 

Cnrrent work on dephosphorylation includes the use of different micellar systems. Scheme 10 illustrates dephosphorylation via novel functional detergents which contain an imidazole ring snbstitnted with an oxime or hydroxamic acid moiety. ... 

In all the bimolecular reactions considered thus far the surfactant has been chemically inert, but a functionalized surfactant will generate a micelle in which reactant is covalently bonded (Scheme 3). The functional groups are basic or nucleophilic, and include amino, imidazole, oximate, hydroxamate, thiolate or hydroxyl [3-6,97-108]. In some cases comicelles of a functional and an inert surfactant have also been used. The reactions studied include deacylation, dephosphorylation, nucleophilic aromatic substitution, and nucleophilic addition to preformed carbocations, and some examples are shown in Scheme 7. 

Mixed micelles of cetyltrimethylammonium bromide and surfactant hydroxamic acids catalyse the hydrolysis of 4-nitrophenyl hexanoate," and the dephosphorylation of 4-nitrophenyl diphenylphosphate. In both cases reaction occurs through the hydroxamate anion and reactivity is again attributed to a lowering of the pK of the hydroxamic acid and an increased nucleophile concentration in the Stern layer. 

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