REACTIONS OF COPPER (I) THIOLATES WITH HALOAROMATICS |
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| Authors: | W. James Frazee Linda J. Johnston Michael E. Peach |
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| Affiliation: | Department of Chemistry , Acadia University , Wolfville, Nova Scotia, Canada |
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| Abstract: | Abstract Recent studies have shown that replacement of I or Br and not C1 or F in haloaromatic compounds occurred when copper (I) thiolates, CuSR, were used as nucleophiles. Some proto debromination was also observed. Conversely using the free thiolate anion, SR?, in solution, replacement of F or C1 rather than I or Br in haloaromatic compounds was observed. These general observations have been confirmed in the reactions of the isomeric dibromotetrafluorobenzenes with copper (I) methanethiolate, copper (I) pentafluorothiophenolate, and the methanethiolate anion. |
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| Keywords: | Phosphonium 1-methyl-3,5,8-trioxabicyclo-[2,2,2]octane-4-methylthiophosphonium ion stereoelectronic effect hydrolysis mechanism |
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