Electrophilic trifluoromethylation of S-hydrogen phosphorothioates |
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Authors: | Santschi Nico Togni Antonio |
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Institution: | Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zu?rich, CH-8093 Zu?rich, Switzerland. |
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Abstract: | A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by (19)F NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors. |
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