Sodium Hypochlorite Pentahydrate as a Reagent for the Cleavage of trans-Cyclic Glycols

Sodium hypochlorite pentahydrate (NaOCl·5H 2 O) can be used toward the efficient glycol cleavage of trans- cyclic glycols, which are generally resistant to this transformation. Interestingly, the reaction of cis -cyclic glycols with NaOCl·5H 2 O is slower than that observed for the corresponding trans -isomer. This trans selectivity is in sharp contrast to traditional oxidants used for glycol cleavage. Acyclic glycols can also react efficiently with NaOCl·5H 2 O to form their corresponding carbonyl compounds in high yield.