An Easy and Efficient Method for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous and Neutral Conditions

Abstract 1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), readily prepared as an orange solid from commercially available DABCO (1,4-diazabicyclo [2.2.2]octane, performs oxidation in anhydrous conditions. Under these conditions, the reagent converts phenylhydrazones, p-phenylhydrazones, semicarbazones, and β-keto sulfoxide hydrazones to the corresponding carbonyl compounds and β-keto sulfoxides respectively, the yields and enantioselectivity are excellent.