Rapid, Stepwise Substitution of Fluorines In 5-Trifluoromethyl-2′-Deoxyuridine by Bisulfite

Abstract On treatment with bisulfite at neutral pH, 5-trifluoromethyl-2′-deoxyuridine (CF3dUR) underwent rapid substitution of the fluorine atoms by bisulfite to give first the monosulfonate and then the disulfonate derivatives. It was shown that the monosulfonate product has reactivity to bisulfite with a potency half that of CF3dUR. These findings demonstrate the stepwise nature of the fluorine release from CF3dUR and constitute evidence that 5-exo-methylene type intermediates are involved in the nucleophile-mediated release of the fluorine from CF3dUR.

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