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Oxidation with dioxiranes : ウィキペディア英語版
Oxidation with dioxiranes
Oxidation with dioxiranes refers to the introduction of oxygen into organic molecules through the action of a dioxirane. Dioxiranes are well known for their oxidation of alkenes to epoxides; however, they are also able to oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.〔Adam, W.; Zhao, C.-G.; Jakka, K. ''Org. React.'' 2007, ''69'', 1. 〕
==Introduction==
Dioxiranes may be produced through the action of KHSO5 on carbonyl compounds. Because of their low-lying σ
*O-O orbital, they are highly electrophilic oxidants and react with unsaturated functional groups, Y-H bonds (yielding oxygen insertion products), and heteroatoms.〔Adam, W.; Curci, R.; Edwards, J. O. ''Acc. Chem. Res.'' 1989, ''22'', 205.〕 The most common dioxiranes employed for organic synthesis are dimethyldioxirane (DMD) and trifluoromethyl-methyldioxirane (TFD). The latter is effective for chemoselective oxidations of C-H and Si-H bonds.〔Asensio, G.; González-Núñez, M. E.; Biox Bernardini, C.; Mello, R.; Adam, W. ''J. Am. Chem. Soc.'' 1993, ''115'', 7250.〕 Although this class of reagents is most famous for the epoxidation of alkenes, dioxiranes have been used extensively for other kinds of oxidations as well.
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File:DioxGen.png


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