The thiolate anion as a nucleophile Part IV. Reactions of some pentafluorophenyl compounds |
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| Authors: | Bonita C. Musial Michael E. Peach |
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| Affiliation: | Chemistry Department, Acadia University, Wolfville, Nova Scotia, BOP 1XO Canada |
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| Abstract: | Direct nucleophilic substitution with sodium methanethiolate of the pentafluorophenyl compounds C6F5X (X = Cl, Br, I. NO2, NH2, CO2H, SC6F5, OMe, OH) has given varying amounts of XC6F4(SMe), XC6F3(SMe)2, C6F4(SMe)2, XC6F2(SMe)3 and C6F2(SMe)4. In some cases cleavage of the aromatic carbon-X bond (X = Br, I, CO2H, SC6F5) forming C6F4(SMe)H and C6F2(SMe)3H, and the O-Me bond forming HOC6F2(SMe)3 was observed. The new compounds isolated have been characterized by elemental analyses, infrared and mass spectra and their stereochemistries have been from their 1H and 19F NMR spectra. |
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