Phase-Vanishing Methodology for Efficient Bromination, Alkylation, Epoxidation, and Oxidation Reactions of Organic Substrates

Nirmal K. Jana and John G. Verkade*
Department of Chemistry, Iowa State University, Ames, Iowa 50011
Org. Lett., 2003, 5 (21), pp 3787–3790
DOI: 10.1021/ol035391b
Publication Date (Web): September 16, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jverkade@iastate.edu

Abstract

Abstract Image

In cases where both reactants in a phase-vanishing reaction are less dense than the fluorous phase, an alternative to the U-tube method is to employ a solvent with greater density than the fluorous phase, such as 1,2-dibromoethane. This modification has been successfully applied to the methylation of a phenol derivative with dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide formation from nitrogen-containing compounds, and S-oxide or sulfone formation from organic sulfides.

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History

  • Published In Issue October 16, 2003
  • Received July 24, 2003

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