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Volumn 39, Issue 27, 1998, Pages 4813-4816

In search for thioketene S-oxide. A vinyl sulfoxide to sulfine rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

EID: 0032474878     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00914-9     Document Type: Article
Times cited : (8)

References (27)
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    • 2. Pelloux-Léon, N.; Arnaud, R.; Ripoll, J.L.; Beslin, P.; Vallée, Y., Tetrahedron Lett., 1997, 38, 1385-1388 ; Vallée, Y.; Ripoll, J.L.; Lafon, C.; Pfister-Guillouzo, G. Can. J. Chem., 1986, 65, 290-291 ; Vallée, Y. Reviews Heteroatom. Chem., 1993, 8, 1-20.
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    • 3. Recent references on the chemistry of sulfines : Braverman, S.; Grinstein, D.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans I, 1998, 103-107. Leriverend, C.; Metzner, P.; Capperucci, A.; Delg'Innocenti, A. Tetrahedron, 1997, 53, 1323-1342. Lacombe, S.; Loudet, M.; Banchereau, E.; Simon, M.; Pfister-Guillouzo, G. J. Am. Chem. Soc., 1996, 118, 1131-1138 ; Baltas, M.; Raouf-Benchekroun, K.; Blic, A.D.; Cazaux, L.; Tisnès, P.; Gorrichon, L., Hussein, K., Barthelat, J.C. Tetrahedron, 1996, 52, 14865-14876.
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    • 3. Recent references on the chemistry of sulfines : Braverman, S.; Grinstein, D.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans I, 1998, 103-107. Leriverend, C.; Metzner, P.; Capperucci, A.; Delg'Innocenti, A. Tetrahedron, 1997, 53, 1323-1342. Lacombe, S.; Loudet, M.; Banchereau, E.; Simon, M.; Pfister-Guillouzo, G. J. Am. Chem. Soc., 1996, 118, 1131-1138 ; Baltas, M.; Raouf-Benchekroun, K.; Blic, A.D.; Cazaux, L.; Tisnès, P.; Gorrichon, L., Hussein, K., Barthelat, J.C. Tetrahedron, 1996, 52, 14865-14876.
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  • 8
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    • 3. Recent references on the chemistry of sulfines : Braverman, S.; Grinstein, D.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans I, 1998, 103-107. Leriverend, C.; Metzner, P.; Capperucci, A.; Delg'Innocenti, A. Tetrahedron, 1997, 53, 1323-1342. Lacombe, S.; Loudet, M.; Banchereau, E.; Simon, M.; Pfister-Guillouzo, G. J. Am. Chem. Soc., 1996, 118, 1131-1138 ; Baltas, M.; Raouf-Benchekroun, K.; Blic, A.D.; Cazaux, L.; Tisnès, P.; Gorrichon, L., Hussein, K., Barthelat, J.C. Tetrahedron, 1996, 52, 14865-14876.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1131-1138
    • Lacombe, S.1    Loudet, M.2    Banchereau, E.3    Simon, M.4    Pfister-Guillouzo, G.5
  • 9
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    • 3. Recent references on the chemistry of sulfines : Braverman, S.; Grinstein, D.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans I, 1998, 103-107. Leriverend, C.; Metzner, P.; Capperucci, A.; Delg'Innocenti, A. Tetrahedron, 1997, 53, 1323-1342. Lacombe, S.; Loudet, M.; Banchereau, E.; Simon, M.; Pfister-Guillouzo, G. J. Am. Chem. Soc., 1996, 118, 1131-1138 ; Baltas, M.; Raouf-Benchekroun, K.; Blic, A.D.; Cazaux, L.; Tisnès, P.; Gorrichon, L., Hussein, K., Barthelat, J.C. Tetrahedron, 1996, 52, 14865-14876.
    • (1996) Tetrahedron , vol.52 , pp. 14865-14876
    • Baltas, M.1    Raouf-Benchekroun, K.2    Blic, A.D.3    Cazaux, L.4    Tisnès, P.5    Gorrichon, L.6    Hussein, K.7    Barthelat, J.C.8
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    • note
    • 2), 4.6 (t, J = 2.5 Hz, CH), 6.46 (s, CH), 7-7.5 (m, ArH).
  • 12
    • 0003476619 scopus 로고    scopus 로고
    • Gordon and Breach Science Publishers, Amsterdam
    • -5 hPa. For an overview of the uses of FVT in organic synthesis, see : Gas phase reactions in organic synthesis, Y. Vallée, Ed., Gordon and Breach Science Publishers, Amsterdam, 1997.
    • (1997) Gas Phase Reactions in Organic Synthesis
    • Vallée, Y.1
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    • 11. Tadashi, I.; Hiroshi, T. J. Org. Chem., 1979, 44, 1002-1003 ; Duchenet, V.; Pelloux, N.; Vallée, Y. Tetrahedron Lett., 1994, 35, 2005-2008 ; Pelloux, N.; Duchenet, V.; Vallée, Y. Phosphorus Sulfur Silicon, 1994, 89, 17-23.
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    • 11. Tadashi, I.; Hiroshi, T. J. Org. Chem., 1979, 44, 1002-1003 ; Duchenet, V.; Pelloux, N.; Vallée, Y. Tetrahedron Lett., 1994, 35, 2005-2008 ; Pelloux, N.; Duchenet, V.; Vallée, Y. Phosphorus Sulfur Silicon, 1994, 89, 17-23.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2005-2008
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  • 19
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    • 11. Tadashi, I.; Hiroshi, T. J. Org. Chem., 1979, 44, 1002-1003 ; Duchenet, V.; Pelloux, N.; Vallée, Y. Tetrahedron Lett., 1994, 35, 2005-2008 ; Pelloux, N.; Duchenet, V.; Vallée, Y. Phosphorus Sulfur Silicon, 1994, 89, 17-23.
    • (1994) Phosphorus Sulfur Silicon , vol.89 , pp. 17-23
    • Pelloux, N.1    Duchenet, V.2    Vallée, Y.3
  • 20
    • 0010423860 scopus 로고    scopus 로고
    • note
    • 2), 7.0-7.3 (m, ArH).
  • 21
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    • note
    • 9), 7.2-7.6 (m, ArH).
  • 23
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    • note
    • 10), 7.3-7.6 (m, ArH).
  • 26
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    • note
    • 18. However, the observation of H-C≡C-S-O-H during the thermolysis of 3 but not during the thermolysis of 2, and the formation of ketone 5 by FVT of 2 but not by FVT of 3, suggest that 2 might not be an intermediate in the reaction pathway from 3 to 1.
  • 27
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    • - and showed that a large basis set has to be used for the geometry optimization in order to feet the experimental data. See : Ruttink, P.J.A.; Burgers, P.C.; Francis, J.T.K. J. Chem. Phys., 1996, 100, 9694-9697.
    • (1996) J. Chem. Phys. , vol.100 , pp. 9694-9697
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.