New Protocol for Oxidation in Water: Micellar Oxidation Systems Composed of Novel Amphiphilic Hydroperoxides

A series of novel amphiphilic hydroperoxides, α-alkoxyalkyl hydroperoxides (α-AHPs) and their related hydroperoxides, were designed and prepared with the intention of developing new oxidizing agents bearing a micelle-forming character in water. After their fundamental physical and interfacial proper...

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Bibliographic Details
Published in:	Langmuir Vol. 20; no. 1; pp. 82 - 89
Main Authors:	Masuyama, Araki, Fukuoka, Kazuyuki, Katsuyama, Naoko, Nojima, Masatomo
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 06-01-2004
Subjects:	Hydrogen-Ion Concentration Micelles Molecular Structure Oxidation-Reduction Peroxides - chemical synthesis Peroxides - chemistry Surface Properties Water - chemistry
Online Access:	Get full text
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Summary:	A series of novel amphiphilic hydroperoxides, α-alkoxyalkyl hydroperoxides (α-AHPs) and their related hydroperoxides, were designed and prepared with the intention of developing new oxidizing agents bearing a micelle-forming character in water. After their fundamental physical and interfacial properties were elucidated, both oxidation of benzyl sulfide and epoxidation of geraniol promoted by these hydroperoxides were investigated in detail under various conditions. Effective oxidation of benzyl sulfide to the corresponding sulfoxide was achieved in aqueous micellar systems composed of α-AHPs 1a−d and a catalytic amount of MoO2(acac)2 at 30 °C. Up to 100% conversion was observed under the optimum conditions. In the case of epoxidation of geraniol in water, the corresponding 2,3-epoxide was selectively formed in good yields. Because the conversion of each substrate in the micellar systems was higher than that in nonmicellar media, the solubilization of substrates into micelles was certainly effective in promoting oxidations of insoluble substrates in aqueous media. Micellar oxidation systems composed of novel amphiphilic hydroperoxides afford a new protocol in order to derive safer conditions under which these reactions may be carried out.
Bibliography:	ark:/67375/TPS-9RCFTC9R-C istex:48F040B946FB8193795D7C66A87DA90DC91889D4 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0743-7463 1520-5827
DOI:	10.1021/la035563d