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Volumn 6, Issue 15, 2004, Pages 2563-2566

Thiophenol-mediated hydrogen atom abstraction: An efficient tin-free procedure for the preparation of cyclopentane derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CYCLOPENTANE; HYDROGEN; THIOPHENOL; THIOPHENOL DERIVATIVE; TRIBUTYLTIN;

EID: 4043161523     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049162g     Document Type: Article
Times cited : (46)

References (52)
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    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
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    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
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    • 0033525025 scopus 로고    scopus 로고
    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
    • (1999) J. Org. Chem. , vol.64 , pp. 819
    • Bogen, S.1    Fensterbank, L.2    Malacria, M.3
  • 39
    • 0030904327 scopus 로고    scopus 로고
    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
    • (1997) Tetrahedron Lett. , vol.53 , pp. 5679
    • Martinez-Grau, A.1    Curran, D.P.2
  • 40
    • 0033574499 scopus 로고    scopus 로고
    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
    • (1999) J. Org. Chem. , vol.64 , pp. 2776
    • Sannigrahi, M.1    Mayhew, D.L.2    Clive, D.L.3
  • 41
    • 0035937263 scopus 로고    scopus 로고
    • See also ref 6c
    • More examples involving intramolecular radical addition to alkynes have been reported: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron 1997, 40, 13797. (b) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (c) Bogen, S.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1999, 64, 819. (d) Martinez-Grau, A.; Curran, D. P. Tetrahedron Lett. 1997, 53, 5679. (e) Sannigrahi, M.; Mayhew, D. L.; Clive, D. L. J. Org. Chem. 1999, 64, 2776. (f) Clive, D. E.; Yang, W.; MacDonald, A. C.; Wang, Z.; Cantin, M. J. Org. Chem. 2001, 66, 1966. See also ref 6c.
    • (2001) J. Org. Chem. , vol.66 , pp. 1966
    • Clive, D.E.1    Yang, W.2    MacDonald, A.C.3    Wang, Z.4    Cantin, M.5
  • 46
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    • note
    • No reaction takes place between alkynes 1 and PhSSPh with AIBN as an initiator.
  • 47
    • 0001279669 scopus 로고
    • We believe that this is a fair comparison of two optimized methods since slow addition of tin hydride using a syringe pump does not give reproducible results with vinyl bromides. Under such conditions, the radical precursors are partially recovered unreacted: Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5900
    • Curran, D.P.1    Kim, D.2    Liu, H.T.3    Shen, W.4
  • 48
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    • note
    • Fragmentation of the translocated radical to ethyl acrylate and a malonyl radical cannot be excluded for this system.


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