Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) persulfate: A mild and efficient oxidant for cleavage of oxime double bonds under anhydrous conditions

Abstract

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)persulfate (BAABCPS) 1 readily prepared as orange solid from commercially available 1,4- diazabicyclo[2.2.2]octane (DABCO) and potassium persulfate, converts oximes and α-sulfinyl oximes to the corresponding carbonyl compounds and β-keto sulfoxides respectively, the yields and enantiomeric purity are excellent.