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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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note
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No reaction takes place between alkynes 1 and PhSSPh with AIBN as an initiator.
-
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47
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0001279669
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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.
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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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49
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For the stereochemistry nomenclature used in this paper, see: Panico, R.; Powell, W. H.; Richer, J.-C. A Guide to IUPAC Nomenclature of Organic Compounds, Recommendation 1993; Blackwell: Oxford, 1993.
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