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Original Articles

Thiol Additions To Dissymmetrical 1,4-Diary Sulfonyl-2-Butynes Regioselectivity And Stereoselectivity

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Pages 275-284 | Received 07 Sep 1985, Published online: 14 Mar 2007

References

  • Thyagarajan , B. S. , Wood , B. F. Jr. and Swynnerton , N. F. 1985 . Phosphorus and Sulfur , 21 : 357
  • Thyagarajan , B. S. , Wood , B. F. Jr. , Glowienka , J. A. and Delgado , P. 1985 . Phosporus and Sulfur , 25 : 1
  • Quintily , U. and Scorrano , G. 1971 . Chem. Commun. , : 260 The acidity of the methyl group in the compounds Ar—SO—CH3 has been shown to be dependent on the substituent on the aromatic ring (see:, No such comparable data are available for aryl methyl sulfones. The only reference to a conjugative interaction between a phenyl sulfonyl function and an -carbanion is that by Bordwell (See: F. G. Bordwell, M. Van Der Puy and N. R. Vanier, J. Org. Chem., 41, 1883, 1885 (1976))
  • Bates , D. K. 1974 . Ph. D. Dissertation University of Idaho .
  • Wadsworth , D. H. and Detty , M. R. 1980 . J. Org. Chem. , 45 : 4611 A variety of trisubstituted olefins show this behavior. Some typical examples were reported by:, b. C. J. M. Stirling, J. Chem. Soc. (1964), 5856; c. M. Voyle, K. S. Kyler, S. Arseniyadis, N. K. Dunlap and D. S. Watt, J. Org. Chem., 48, 470 (1983); d. M. Mikolajczk, S. Grzejszczak, A. Chefcznska and A. Zatorski, J. Org. Chem., 44, 2967 (1979); In addition, the “additive increments method” estimates that the absorption by the vinylic proton in the E isomer is between 0.2–1.0 ppm more shielded than the same absorption by the Z isomer in vinyl sulfides with similar structure. (See C. Pascal, J. Meier and W. Simon, Helv. Chim. Acta, 49, 164 (1966)

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