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Volumn , Issue 15, 1996, Pages 1811-1812

Unusual mechanism of hydrolysis of the tosyl cyanide-cyclopentadiene adduct to the lactam 2-azabicyclo[2.2.1]hept-5-en-3-one

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Indexed keywords


EID: 1842577821     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001811     Document Type: Article
Times cited : (2)

References (18)
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    • ed. S. Patai and Z. Rappoport, Interscience, London
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    • Rüffer, U.1    Breitmair, E.2
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    • U. Rüffer and E. Breitmair, Synthesis, 1989, 623; S. M. Weinreb and R. R. Smith, Tetrahedron, 1982, 38, 3087; A. M. Van Leusen and J. C. Jagt, Tetrahedron Lett., 1970, 971; P. G. Pews, E. B. Nyquist and F. P. Corson, J. Org. Chem., 1970, 35, 4096.
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    • U. Rüffer and E. Breitmair, Synthesis, 1989, 623; S. M. Weinreb and R. R. Smith, Tetrahedron, 1982, 38, 3087; A. M. Van Leusen and J. C. Jagt, Tetrahedron Lett., 1970, 971; P. G. Pews, E. B. Nyquist and F. P. Corson, J. Org. Chem., 1970, 35, 4096.
    • (1970) Tetrahedron Lett. , pp. 971
    • Van Leusen, A.M.1    Jagt, J.C.2
  • 6
    • 0000573902 scopus 로고
    • U. Rüffer and E. Breitmair, Synthesis, 1989, 623; S. M. Weinreb and R. R. Smith, Tetrahedron, 1982, 38, 3087; A. M. Van Leusen and J. C. Jagt, Tetrahedron Lett., 1970, 971; P. G. Pews, E. B. Nyquist and F. P. Corson, J. Org. Chem., 1970, 35, 4096.
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    • note
    • 3), 4.42 (1 H, m, HCC=N), 5.39 (1 H, m, HC=N), 6.80 (2 H, m, HC=CH), 7.37 and 7.78 (each 2 H. d, J 9 Hz, ArH's).
  • 12
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    • S. J. C. Taylor, A. G. Sutherland, C. Lee, R. Wisdom, S. Thomas, S. M. Roberts and C. Evans, J. Chem. Soc., Chem. Commun., 1990, 1120; C. F. Palmer, K. P. Parry and S. M. Roberts, J. Chem, Soc., Perkin Trans. 1, 1991, 485; C. F. Palmer, K. P. Parry, S. M. Roberts and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1991, 2051; 1992, 1021.
    • (1991) J. Chem, Soc., Perkin Trans. 1 , pp. 485
    • Palmer, C.F.1    Parry, K.P.2    Roberts, S.M.3
  • 13
    • 37049070345 scopus 로고
    • S. J. C. Taylor, A. G. Sutherland, C. Lee, R. Wisdom, S. Thomas, S. M. Roberts and C. Evans, J. Chem. Soc., Chem. Commun., 1990, 1120; C. F. Palmer, K. P. Parry and S. M. Roberts, J. Chem, Soc., Perkin Trans. 1, 1991, 485; C. F. Palmer, K. P. Parry, S. M. Roberts and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1991, 2051; 1992, 1021.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 2051
    • Palmer, C.F.1    Parry, K.P.2    Roberts, S.M.3    Sik, V.4
  • 14
    • 1842569928 scopus 로고
    • S. J. C. Taylor, A. G. Sutherland, C. Lee, R. Wisdom, S. Thomas, S. M. Roberts and C. Evans, J. Chem. Soc., Chem. Commun., 1990, 1120; C. F. Palmer, K. P. Parry and S. M. Roberts, J. Chem, Soc., Perkin Trans. 1, 1991, 485; C. F. Palmer, K. P. Parry, S. M. Roberts and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1991, 2051; 1992, 1021.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 1021
  • 16
    • 1842465351 scopus 로고    scopus 로고
    • note
    • 18O, 112.0648.
  • 17
    • 1842465352 scopus 로고    scopus 로고
    • note
    • 3O). Other minor products were also detected which were consistent with the fact that sulphinate 7 undergoes disproportionation.


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