Oxidative cleavage of lactams in water using dioxiranes: an expedient and environmentally-safe route to omega-nitro acids

By taking advantage of the appreciable stability of dioxiranes in water, a safe yet efficient route to ?-nitro acids by oxidation of lactams of various ring size under mild conditions has been reported. In essentially all the cases examined, reactions proceed selectively to afford products in remarkable high yields (up to 99%) and with high purity (94-99%). Also, an interesting example of higher reaction selectivity in water than in organic solvent (acetonitrile) is discussed.