AN EASY AND EFFICIENT METHOD FOR CLEAVAGE OF CARBON-NITROGEN DOUBLE-BONDS UNDER NONAQUEOUS AND NEUTRAL CONDITIONS

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), re adily prepared as an orange solid from commercially available DABCO (1 ,4-diazabicyclo [2.2.2]octane, performs oxidation in anhydrous conditi ons. Under these conditions, the reagent converts phenylhydrazones, p- phenylhydrazones, semicarbazones, and beta-keto sulfoxide hydrazones t o the corresponding carbonyl compounds and beta-keto sulfoxides respec tively, the yields and enantioselectivity are excellent.