Kinetics of Cleavage of Thiophosphates and Phosphonothioates by Micellar Iodosocarboxylates and Copper Metallomicelles

o -Iodosobenzoate ( 1, IBA) and 2,3-iodosonaphthoate ( 2, INA) in aqueous cetyltrimethylammonium chloride ((CTA)Cl) micelles, as well as copper metallomicelles 14, all at pH 8, cleave phosphonothioates ( 11 and 12 ), the thiophosphate parathion ( 10 ), phosphonate 13, and phosphate 4 (paraoxon). The factors for the kinetic advantages in the cleavages of 12 and parathion range from 10 3 to 10 4 . Although catalytic turnover of the iodoso reagents is not observed with the thio substrates and is slow with paraoxon, excess IBA/(CTA)Cl destroys paraoxon and parathion with reaction half-lives of 3.0 and 7.7 min, respectively, at pH 8.0 and 25 °C. The cleavages of 12 and parathion by IBA or INA involve an initial hydrolytic step followed by oxidation of the sulfur-containing fragment. Cleavages of 12 and parathion by o -iodoxybenzoate ( 1X, IBX) in (CTA)Cl micelles are much slower than the comparable reactions mediated by IBA, INA, and 14 .