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Tin(IV) Chloride Promoted Reaction of Oxiranes with Hydrogen Peroxide

Xing Yan, Chunhua Qiao*, Zhongwu Guo

*College of Pharmaceutical Science, Soochow University, 199 Ren Ai Road, Suzhou 215123, P. R. of China, Email:

X. Yan, C. Qiao, Z. Guo, Synlett, 2013, 24, 502-506.

DOI: 10.1055/s-0032-1318213

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Substituted oxiranes were readily transformed to the corresponding β-hydroxyhydroperoxides in good yields in ethereal H2O2 system with SnCl4 as a catalyst. Alternatively, the use of a stoichiometric amount of SnCl4 leads to a rearrangement of the oxiranes to aldehydes. A subsequent addition of ethereal H2O2 solution achieves primary gem-dihydroperoxides in moderate yields.

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Key Words

SnCl4, oxiranes, β-hydroxyhydroperoxides, gem-dihydroperoxides, peroxides

ID: J60-Y2013-0600