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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 2
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Original Articles

An Efficient Preparation of Diethyl Phenylsulf Onylmethylphosphonate

Pages 139-147 | Published online: 05 Dec 2006

References

  • Van Leusen , A. M. , Reith , B. A. , Iedema , A. J.W. and Strating , J. 1972 . Rec. Trav. Chim. Pays-Bas , 91 : 37
  • Ito , Y. , Okano , M. and Oda , R. 1967 . Tetrahedron , 23 : 2137 Other investigators have also encountered difficulty inducing condensation between related sulfonyl-stabilized phosphonium ylids and aldehydes. See, for example:
  • Mikolajczyk , M. , Grezejszczak , S. , Midura , W. and Zatorski , A. 1975 . Synthesis , : 278 Mikolajczyk, M.; Grezejszczak, S.; and Zatorski, A. Tetrahedron Lett., 1975, 3757. Posner, G.H. and Brunelle, D.J. J. Org. Chem., 1972, 37, 3547. Flitsch, W. and Lubisch, W. Chem. Ber., 1984, 117, 1424
  • Ellingsen , P. O. and Undheim , K. 1979 . Acta Chem. Scand. , B33 : 528
  • Wadsworth , W. S. Jr. 1977 . Org. React. , 25 : 73 For an excellent review, see:
  • Arbuzov , B. A. and Bogonostseva , N. P. 1957 . J. Gen. Chem., USSR , 27 : 2419 Zhur. Obstich. Khim., 1957, 27, 2360
  • Green , M. 1963 . J. Chem. Soc. , : 1324
  • Mikolajczyk , M. and Zatorski , A. 1973 . Synthesis , : 669
  • Shahak , I. and Almog , J. 1970 . Synthesis , : 145
  • Paquette , L. A. 1977 . Org. React. , 25 : 1 For a discussion of the recalcitrance of α-halo sulfones to undergo nucleophilic substitution, see: and references cited therein
  • Commercially available from the Aldrich Chemical Company or Parish Chemical Company
  • Previous investigators 7,8 reported heating a 1:1 mixture of triethyl phosphite and chloromethyl phenyl sulfide to provide phosphonate 5 in 70% yield. We have found that use of an excess of triethylphosphite leads to a significant improvement in the yield of this reaction
  • Trost , B. M. and Curran , D. P. 1981 . Tetrahedron Lett. , 22 : 1287
  • de Jong , B. E. , de Koning , H. and Huisman , H. O. 1981 . J. Royal Netherlands Chem. Soc. , 100 : 410 The oxidation of 5 to 4a with m-chloroperbenzoic acid was recently reported:

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