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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, Email: jverkadeiastate.edu

N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5, 3787-3790.

DOI: 10.1021/ol035391b (free Supporting Information)


Abstract

Use of a solvent with greater density than the fluorous phase is an alternative to the U-tube method in phase-vanishing reactions in cases where both reactants are less dense than the fluorous phase. This method 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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Key Words

Aryl Bromides, Allyl Bromides, Aryl Ethers, Epoxides, N-Oxides, Sulfones, MCPBA, Prilezhaev Reaction


ID: J54-Y2003-970