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Synthesis 1997; 1997(8): 866-868
DOI: 10.1055/s-1997-1287
short paper
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Elimination of Sulfur Dioxide in Alkanesulfonamides. Formation of 2-Arylhydrazono-3,3,3-trifluoropropylamines from 2-Arylhydrazono-3,3,3-trifluoropropanesulfonamides

Masahiko Takahashi* , Shigeru Muta
  • *Department of Materials Science, Faculty of Engineering, Ibaraki University, Hitachi, Ibaraki 316, Japan, Fax +81(294)344668
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Publication Date:
31 December 2000 (online)

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Treatment of 2-arylhydrazono-3,3,3-trifluoropropanesulfonamides 3 with base gave 2-arylhydrazono-3,3,3-trifluoropropylamines 5 in moderate yields. Thiaziridinium 1,1-dioxide intermediates 10 are postulated in this new elimination reaction of sulfur dioxide in alkanesulfonamides.

sulfur dioxide - elimination - 3,3,3-trifluoropropanesulfonamide - 3,3,3-trifluoropropylamine - thiaziridinium - 1,1-dioxide