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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 10
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Original Articles

A Convenient Procedure for the Reduction of Sulfones to Sulfoxides

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Pages 923-930 | Received 12 Jul 1979, Published online: 06 Dec 2006

References

  • Still , I. W. J. , Hasan , S. K. and Turnbull , K. 1978 . Can. J. Chem. , 56 : 1423
  • Drabowicz , J. , Numata , T. and Oae , S. 1977 . Org. Prep. Proced. Int. , 9 : 63
  • Gardner , J. N. , Kaiser , S. , Krubiner , A. and Lucas , M. 1973 . Can. J. Chem. , 51 : 1419
  • Benson , S. W. 1978 . Chem. Rev. , 78 : 23
  • Chalkley , G. R. , Snodin , D. J. , Stevens , G. and Whiting , M. C. 1970 . J. Chem. Soc. (C) , : 682
  • Santaniello , E. , Ponti , F. and Manzocchi , A. 1978 . Synthesis , : 891
  • Since a competing thermal process of the p-chlorobenzene-diazonium salt is the Schiemann reaction to produce p-chlorofluorobenzene, we cannot completely rule out the possibility that diborane, produced from the reaction of borohydride with BF3, is the actual reducing agent. Stoichiometric and mechanistic considerations, however, make this much less likely in our view
  • Shimagaki , M. , Tsuchiya , H. , Ban , Y. and Oishi , T. 1978 . Tetrahedron Lett. , : 3435 In this paper, which appeared after we had initiated the present investigation, the authors allude to the possibility of selectively reducing aryloxysulfoxonium salts derived from sulfones to sulfoxides, but report only one example, the reduction of the salt derived from phenyl methyl sulfone and benzene-diazonium fluoroborate with α-toluenethiol or liquid sulfur dioxide-pyridine
  • Chalkley , G. R. , Snodin , D. J. , Stevens , G. and Whiting , M. C. 1978 . J. Chem. Soc. Perkin I , : 1580 The reactions of aryloxysulfoxonium salts with a variety of nucleophiles other than hydride donors have recently been reported
  • Vogel , A. I. 1956 . “Practical Organic Chemistry, , 3rd Edition , 611 London, , England : Longmans, Green and Co., Ltd. .
  • Ether or chloroform could be used here to almost equal advantage

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