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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 14
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Original Articles

Sulfinates as Nucleophiles for the Ring-Opening of Epoxides: A Convenient Route to β-Hydroxysulfones

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Pages 1103-1110 | Published online: 05 Dec 2006

References

  • Wildeman , J. and van Leusen , A. M. 1979 . Synthesis , : 733
  • Huston , R. C. and Bostwick , C. O. 1948 . J. Org. Chem. , 13 : 331
  • Detty , M. R. and Seidler , M. D. 1982 . Tetrahedron Lett. , 23 : 2543
  • Culvenor , C. C. J. , Davies , W. and Heath , N. S. 1949 . J. Chem. Soc. , : 278
  • Culvenor , C. C. J. , Davies , W. and Savige , W. E. 1949 . J. Chem. Soc. , : 2198
  • Weinstock , J. , Pearson , R. G. and Bordwell , F. G. 1956 . J. Am. Chem. Soc. , 78 : 3468
  • Hentrich , W. and Gündel , W. U.S. 2, 378, 551 . June 19, 1945 . Chem. Abs., 1945, 39, 4081
  • The only aliphalic sulfinate salt tried, potassium trifluoromethanesulfinate, was also in this category and did not react
  • The reaction with ethylene oxide (b.p. 16°C) was run at 0°C
  • Hopkins , P. B. and Fuchs , P. L. 1978 . J. Org. Chem. , 43 : 1208
  • Regis , R. R. and Doweyko , A. M. 1982 . Tetrahedron Lett. , 23 : 2539 Cf.
  • Weast , R. C. , ed. 1981 . “CRC Handbook of Chemistry and Physics” , 61st Edn. , Boca Raton, FL : CRC Press Inc. .
  • Crumbie , R. L. , Deol , B. S. , Nemorin , J. E. and Ridley , D. D. 1978 . Aust. J. Chem. , 31 : 1965
  • The previous authors12 found a value of δ 2.69 for the OH proton. Our assignment of δ 3.1 for this proton is based on the disappearance of the signal on shaking with D2O. The chemical shift of the OH proton does not vary with concentration, presumably due to intramolecular hydrogen bonding

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