Please use this identifier to cite or link to this item:
Type: Artigo de periódico
Title: Homogeneously Catalyzed Epoxidation Of α,β-unsaturated Ketones Using Simple Aluminum Salts And Aqueous H2o2-is It Possible?
Author: Rinaldi R.
de Oliveira H.F.N.
Schumann H.
Schuchardt U.
Abstract: Simple aluminum salts activate hydrogen peroxide towards α,β-unsaturated ketones, affording as major products α,β-epoxyketones. The pathway of this reaction involves the interaction between [Al(H2O)6]3+ and H2O2, through hydrogen bonds, in the second-coordination sphere. This interaction enhances the proton exchange between non-coordinated water and hydrogen peroxide, as detected by 1H NMR experiments. By this means, the hydroperoxide anion, formed as reactive intermediate in the proton exchange between H2O and H2O2, can be trapped by α,β-unsaturated ketones. Surprisingly, this pathway is not followed when diethylmaleate is used as substrate. In this case, the radical addition of THF to the C{double bond, long}C bond of diethylmaleate takes place with high selectivity, affording 2-(THF)-derivatives with high yields. © 2009 Elsevier B.V. All rights reserved.
Rights: fechado
Identifier DOI: 10.1016/j.molcata.2009.04.005
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File Description SizeFormat 
2-s2.0-67349253855.pdf413.34 kBAdobe PDFView/Open

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.