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Original Articles

STEREOSPECIFIC INTERCONVERSION OF THIO- AND SELENOPHOSPHORYL COMPOUNDS

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Pages 321-325 | Received 05 Jul 1982, Accepted 12 Nov 1982, Published online: 13 Dec 2006

References

  • Horner , L. and Winkler , H. 1964 . Tetrahedron Letters , : 175
  • Zon , G. , DeBruin , K. E. , Naumann , K. and Mislow , K. 1969 . J. Amer. Chem. Soc. , 91 : 7023 N. J. De'ath, K. Ellis, D. J. H. Smith and S. Trippett, J.C.S. Chem. Commun., 1971, 714; K. E. DeBruin and D. M. Johnson, J. Amer. Chem. Soc., 95, 4675 (1973)
  • Omelanczuk , J. and Mikolajczyk , M. 1979 . J. Amer. Chem. Soc. , 101 : 7292 J. Omelanczuk, W. Perlikowska and M. Mikolajczyk, J.C.S. Chem. Commun., 1980, 24; M. Mikolajczyk, Pure and Appl. Chem., 52, 959 (1980)
  • Horner , L. 1980 . Pure and Appl. Chem. , 52 : 843
  • In a typical experiment the reaction of 1b with NaSH afforded triphenylphosphine sulphide (2), triphenylphosphine oxide, methyltriphenylphosphonium trifluoromethanesulphonate and triphenylphosphine in 57, 11, 17 and 15% yield, respectively. An explanation for the formation of by-products will be given in a full paper
  • Stec , W. J. , Okruszek , A. and Michalski , J. 1971 . Angew. Chem. , 83 : 494
  • The reaction of (+)-(R)-1d, [α]589 + 31.4°, with NaSH in methanol, e.g. under homogeneous conditions, gave (+)-(R)-sulphide (4) in 64% yield having [α]589 + 17.5° (80% e.e.)
  • Tsurugi , J. , Nakabayashi , T. and Ishihara , T. 1965 . J. Org. Chem. , 30 : 2707 For a similar reaction between achiral trivalent phosphorus compounds and alkyl or aryl hydrodisulphides see: T. Nakabayashi, S. Kawamura, T. Kitao and J. Tsurugi, J. Org. Chem., 31, 861 (1966); T. Nakabayashi, J. Tsurugi, S. Kawamura, T. Kitao, M. Ui and M. Nose, J. Org. Chem., 31, 4174 (1966)

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