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. Acyclic glycols can also react efficiently with NaOCl·5HO to form their corresponding carbonyl compounds in high yield.
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| http://dx.doi.org/10.1021/acs.joc.9b01132 | DOI Listing |
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