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L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
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L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
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For a preliminary report of this work see: P. C. Montevecchi, M. L. Navacchia, P. Spagnolo, Tetrahedron Lett. 1997, 38, 7913-7916.
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37
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For previous reports on thiol-mediated radical cyclizations of alkynes see refs.(([9b][9c][9g][9h])). See also: C. A. Broka, D. E. C. Reichert, Tetrahedron Lett. 1987, 28, 1503-1506 and L. El Kaim, A. Gacon, A. Perroux, Tetrahedron Lett. 1998, 39, 371-374.
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For previous reports on thiol-mediated radical cyclizations of alkynes see refs.(([9b][9c][9g][9h])). See also: C. A. Broka, D. E. C. Reichert, Tetrahedron Lett. 1987, 28, 1503-1506 and L. El Kaim, A. Gacon, A. Perroux, Tetrahedron Lett. 1998, 39, 371-374.
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44
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2742593510
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note
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Arenethiols are more powerful hydrogen donors than alkanethiols as a result of their lower S-H bond strength (80 and 88 kcal/mol, respectively). The syringe pump technique allowed the use of a very low concentration of benzenethiol 1c.
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45
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46
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[10g]; see also: O. Ito, R. Omori, M. Matsuda, J Am. Chem. Soc. 1982, 104, 3934-3937, and S. W. Benson, Chem. Rev. 1978, 78, 23-35.
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0002226173
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[10g]; see also: O. Ito, R. Omori, M. Matsuda, J Am. Chem. Soc. 1982, 104, 3934-3937, and S. W. Benson, Chem. Rev. 1978, 78, 23-35.
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2742522164
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