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

Xing Yan; Chunhua Qiao; Zhongwu Guo

doi:10.1055/s-0032-1318213

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(4): 502-506
DOI: 10.1055/s-0032-1318213

letter

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

Xing Yan

^aCollege of Pharmaceutical Science, Soochow University, 199 Ren Ai Road, Suzhou 215123, P. R. of China Fax: +86(512)65882089 eMail: qiaochunhua@suda.edu.cn

,

Chunhua Qiao*

^aCollege of Pharmaceutical Science, Soochow University, 199 Ren Ai Road, Suzhou 215123, P. R. of China Fax: +86(512)65882089 eMail: qiaochunhua@suda.edu.cn

,

Zhongwu Guo

^bDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA

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Abstract

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Abstract

A group of substituted oxiranes were readily transformed to the corresponding β-hydroxyhydroperoxides (HHP) in good yields in ethereal SnCl₄–H₂O₂ system in which SnCl₄ acts as catalyst. Alternatively, treating oxiranes with SnCl₄ first, followed by addition of ethereal H₂O₂ solution achieved primary gem-dihydroperoxides (DHP) in moderate yields. In the case of preparing DHP, SnCl₄ first promoted the rearrangement of oxiranes to aldehydes, followed by condensation with hydrogen peroxide to provide DHP as final products.

Key words

SnCl₄ - oxirane - β-hydroxyhydroperoxide - gem-dihydroperoxide

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Referenzen

References and Notes
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