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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 8
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Original Articles

Improved Oxidation of the Sulfenamide Functionality: Efficient Synthesis of 6-Ethoxy-2-Benzothiazolesulfonamide

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Pages 899-903 | Published online: 19 Dec 2006

References

  • Foye , W. O. 1981 . Principles of Medicinal Chemistry , Philadelphia : Lea and Febiger .
  • Andersen , K. K. 1979 . Comprehensive Organic Chemistry , Edited by: Barton , D. and Ollis , W. D. Vol. 3 , 19 New York : Pergamon Press . Ch. 11
  • Glander , I. and Golloch , A. 1975 . J. Fluorine Chem. , 5 : 83
  • Glass , R. S. and Swedo , R. J. Synthesis , 1977 798
  • Brit. Pat. . 795, 714 . 1958 . to Upjohn
  • Woltersdorf , O. W. Jr. U. S. Pat. . 4, 416, 890 .
  • Woltersdorf , O. W. Jr. , Michelson , S. R. , Sondey , M. and Schwam , H. U. S. Pat. . 4, 386, 098 .
  • Korman , J. 1958 . J. Org. Chem. , 23 : 1768
  • For other reported oxidants of the sulfenamide functionality see:.
  • Davis , F. A. , Nadir , U. K. and Kluger , E. W. J. Chem. Soc., Chem. Commun. , 1977 25
  • Huang , S.-L. and Swern , D. 1979 . J. Org. Chem. , 44 : 2510
  • Haake , M. , Gebbing , H. and Benack , H. Synthesis , 1979 97
  • Johnson , C. R. and Wambagans , A. 1979 . J. Org. Chem. , 44 : 2278
  • Hydrogen peroxide and t-butyl peroxide gave no oxidation. Sodium hypochlorite under phase-transfer conditions (CH2Cl2-H2O, nBu4NBr) and Oxone® provided low yields of 1; 17% and 14% respectively. Sodium meta-periodate led to degradation of the sulfenamide.

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