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Synlett 1992; 1992(11): 911-913
DOI: 10.1055/s-1992-21539
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A Simple and Efficient Preparation of N,N-Disubstituted (1-Alkyne)- or (E)-(1-Alkene)sulfinamides and their Conversion into the Corresponding Sulfinates or Sulfonamides1

Jean-Bernard Baudin* , Sylvestre A. Julia, Yuan Wang
  • *Laboratoire de Chimie, Ecole Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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Publication Date:
08 March 2002 (online)

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Treatment of (1-piperidine)- or (4-morpholine)sulfinyl chloride with unsaturated lithio-, bromomagnesio- or diisobutylalumino-derivatives afforded the title sulfinamides 4 and 5. The 1-alkyne sulfinamides 4 were smoothly reduced with lithium aluminium hydride to furnish (E)-1-alkenylsulfinamides. The unsaturated sulfinamides 4,5 and 8 were converted into the corresponding sulfinates 6, 7 and 9 by treatment with alcohols in the presence of boron trifluoride etherate. Oxidation of 4, 5 and 8 yielded the unsaturated sulfonamides 11, 12 and 13.

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