Iodine as a catalyst for efficient conversion of ketones to gem-dihydroperoxides by aqueous hydrogen peroxide

Katja Zmitek; Marko Zupan; Stojan Stavber; Jernej Iskra

doi:10.1021/ol060590r

Iodine as a catalyst for efficient conversion of ketones to gem-dihydroperoxides by aqueous hydrogen peroxide

Org Lett. 2006 Jun 8;8(12):2491-4. doi: 10.1021/ol060590r.

Authors

Katja Zmitek¹, Marko Zupan, Stojan Stavber, Jernej Iskra

Affiliation

¹ Laboratory of Organic and Bioorganic Chemistry, Jozef Stefan Institute, Jamova 39, Ljubljana, Slovenia.

PMID: 16737296
DOI: 10.1021/ol060590r

Abstract

Iodine has been shown to be an efficient catalyst for the selective dihydroperoxidation of ketones with aqueous hydrogen peroxide. Ketones were directly converted to their corresponding gem-dihydroperoxides using a "green" oxidant (30% aq H(2)O(2)) and a simple catalyst (iodine) under neutral conditions in acetonitrile. The yield of hydroperoxidation of various cyclic ketones was 60-98% including androstane-3,17-dione, and acyclic ketones were converted with a similar efficiency. [reaction: see text]