MECHANISM OF PHOSPHINYLOXYSULFONATE FORMATION ON PERACID OXIDATION OF N,N,N',N'-TETRASUBSTITUTED PHOSPHORODIAMIDOTHIOLATES

Article abstract of DOI:10.1016/0040-4039(91)80003-O

Peracid oxidation of N,N,N',N'-tetrasubstituted phosphorodiamidothiolates in chloroform yields, among other products, the corresponding phosphinyloxysulfonates via the alkylsulfonic acids by both S_N¹ and S_N² type mechanisms with their relative contribution determined by the concentration of the sulfonic acid.The first products (t_1/2 10-50 min) in the oxidation sequence are tentatively assigned by 1H, 13C and 31P NMR as the phosphorothiolate sulfoxide and sulfone.