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

Sodium hypochlorite pentahydrate (NaOCl·5HO) 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·5HO is slower than that observed for the corresponding trans-isomer. This trans selectivity is in sharp contrast to traditional oxidants used for glycol cleavage.