NONRADICAL TETRABUTYLAMMONIUM MONOPERSULFATE OXIDATION OF HYDROCARBONS CATALYZED BY [MN(3)O(4)BIPY(4)(H2O)(2)](CLO4)(4)

Tetrabutylammonium monopersulfate (2NBu(4)HSO(5) . NBu(4)HSO(4) . (NBu (4))(2)SO4) is an effective primary oxidant with a high tendency to pr omote oxo transfer rather than radical pathways in catalysis. Nonradic al hydrocarbon oxidation is seen with the complex [Mn(3)O(4)bipy(4)(H2 O)(2)](ClO4)(4) as catalyst as indicated by mechanistic studies; this contrasts with the radical pathways found for the same catalyst with t -BuOOH as the primary oxidant. The catalyst is robust, giving up to 15 000 catalytic turnovers, and very efficient, the rate of 1-alkene epox idation being 4000 turnovers/h.