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:
jverkade
iastate.edu
N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5, 3787-3790.
DOI: 10.1021/ol035391b
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
