Selective oxidation of spirolactone-related sulfides to corresponding sulfoxides and sulfones by hydrogen peroxide in the presence of N-hydroxysuccinimde

Spirolactone-related sulfides were oxidized to corresponding sulfoxides and sulfones selectively and in high yield by hydrogen peroxide using N-hydroxysuccinimide as an efficient catalyst under metal-free conditions. Sulfoxides were obtained without over-oxidation to sulfones in acetone under reflux condition whereas sulfones were obtained in methanol at room temperature. Both processes were compatible with the presence of sensitive groups including ketones, alkenes, hydroxyl groups and benzylic carbons under our conditions. (c) 2007 Elsevier B.V. All rights reserved.