The thiolate anion as a nucleophile Part III. Reactions with various fluorobenzenes |
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Authors: | Michael E. Peach Ashley M. Smith |
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Affiliation: | Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada |
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Abstract: | The reactions of the fluorobenzenes, C6F5H, o-C6H2F4, m-C6H2F4, p-C6H2F4, 1,3,5-C6F3H3, 1,2,4-C6F3H3, o-C6F2H4, m-C6F2H4, p-C6F2H4 and C6F5H with thiolate anion nucleophiles RS? (primarily MeS?), have been studied in ethylene glycol/pyridine mixtures as a solvent. Multiple replacement of fluorine atoms was observed in the more highly fluorinated compounds, but in all cases two aromatic fluorine atoms were not replaced. Difluorobenzene and fluorobenzene did not react. The product orientations have been deduced from their NMR spectra. The mass spectra of the isomeric products C6F2H3(SMe), C6F3H2(SMe) and C6F2H2(SMe)2 have been examined. |
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