Sulphol-3-ene can be deprotonated with sodium hydride in DMF to form the α-anion which reacts with various alkyl halides to give the 2-alkylsulpholenes. This approach provides a regiospecific preparation of disubstituted sulphol-3-enes and sulphol-2-enes.
T. Chou, H. Tso and L. Chang, J. Chem. Soc., Perkin Trans. 1, 1985, 515 DOI: 10.1039/P19850000515
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