Regioselective Approach to β-Peroxyl Alcohols and Ethers from Alkenes
Huan Xu1, Xinyao Lou1, Junrang Xie1
1Key Laboratory of Coal Conversion and New Carbon Materials of Hubei Province, College of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, PR China.
Abstract:
A different regioselective three-component reaction of alkenes, oxygen sources, and hydroperoxides mediated by ammonium iodine to α-oxyperoxidates has been developed. Mechanistic studies demonstrated that regioselective radical addition and subsequent SN2 nucleophilic substitution were possible for the formation of products. In addition to the traditional pathway of SN2 reaction, that is, where nucleophiles attack the α-C atoms at the back side, an additional unusual transition configuration with the H2O molecule attacking the α-C atom at the front side was obtained.
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