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Synlett 2001; 2001(3): 0371-0373
DOI: 10.1055/s-2001-11406
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Stereoselective Synthesis of (Z)-α-Organothiovinyltosylates and their Application in the Synthesis of Highly Functionalized Vinylic Sulfides

Antonio L. Braga* , Daniel J. Emmerich, Claudio C. Silveira, Tales L. C. Martins, Oscar E. D. Rodrigues
  • *Departamento de Química, Universidade Federal de Santa Maria, Br-97105-900, Santa Maria, RS, Brazil
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Publikationsdatum:
31. Dezember 2001 (online)

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Thioacetylenes 1 afford, upon treatment with p-toluenesulfonic acid in dichloromethane, (O,S)-ketene acetals 2 which can act as useful α-(organothio)vinyl carbocation equivalents, opening a novel route to functionalized vinylic sulfides.

(O,S)-ketene acetals - carbocation equivalents - regioselective - addition - vinylsulfides