Chinese Journal of Organic Chemistry >
Radical Oxidation of α-Hydroxyl Ester Initiated by Sodium Hypochlorite
Received date: 2019-01-15
Revised date: 2019-03-12
Online published: 2019-03-29
Sodium hypochlorite has been used as a green oxidant in oxidation of alcohols. However, the oxidation of a-hydroxyl ester via sodium hypochloriteis difficult under the same conditions. Herein, an efficient method is developed for the oxidation of a-hydroxyl ester with sodium hypochlorite in the presence of hydrogenbromide. In this case, a reaction mechanism was proposed with the formation of free radicals as reactive intermediates, which was different from the mechanism of traditional Stevens oxidation. The method is also applied to the oxidation of common secondary alcohol and has good selectivity for multi-hydroxyl compounds.
Key words： sodium hypochlorite; green; radical oxidation; selectivity
Wang Maochang , Zhang Baohua , Ding Kai . Radical Oxidation of α-Hydroxyl Ester Initiated by Sodium Hypochlorite[J]. Chinese Journal of Organic Chemistry, 2019 , 39(7) : 1996 -2000 . DOI: 10.6023/cjoc201901019
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