Abstract
The rationalization of thermodynamic and kinetic data of silane/silyl radical systems allows the characterization of a class of silanes as new reducing agents. In fact, tris(trimethylsilyl)silane and trialkylmercaptosilanes would appear to offer an attractive alternative to tributyltin and tributylgermanium hydrides respectively in radical chain reactions.
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References
For a recent review see: B. Giese, Angew. Chem. Int. Ed. Engl., 24, 553 (1985).
D.F. McMillen, and D.M. Golden, Annu. Rev. Phys. Chem., 33, 493 (1982).
R. Walsh, Acc. Chem. Res., 14, 246 (1981).
C. Chatgilialoglu, K.U. Ingold, J. Lusztyk, A.S. Nazran, and J.C. Scaiano, Organometallies, 2, 1332 (1983).
J.M. Kanabus-Kaminska, J.A. Hawari, D. Griller, and C. Chatgilialoglu, J. Am. Chem. Soc., 109, 5267 (1987).
J. Murray, J. Am. Chem. Soc, 106, 5842 (1984) and 107, 7271 (1985).
C. Chatgilialoglu, and S. Rossini, Bull. Soc. Chim. Fr., in press.
C. Chatgilialoglu, and G. Seconi, unpublished results.
M.P. Doyle, C.C. McOsker, and C.T. West, J. Org. Chem., 41, 1393 (1976).
J. Lusztyk, B. Maillard, and K.U. Ingold, J. Org. Chem., 51, 2457 (1986) and references therein.
C. Chatgilialoglu, D. Griller, and M. Lesage, J. Org. Chem., in press.
C. Chatgilialoglu, D. Griller, and M. Lesage, J. Org. Chem., Submitted for publication.
C. Chatgilialoglu, K.U. Ingold, and J.C. Scaiano, J. Am. Chem. Soc., 103, 7739 (1981).
C. Chatgilialoglu, D. Griller, and M. Lesage, studies are currently in progress.
B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986.
E.J. Corey, and J. Williams Suggs, J. Org. Chem., 40, 2554 (1975).
C. Chatgilialoglu, D. Griller, and M. Lesage, Italian Patent: 48150A87 (1987).
J. Lusztyk, B. Maillard, S. Deycard, D.A. Lindsay, and K.U. Ingold, J. Org. Chem., 52, 3509 (1987); K.U. Ingold, J. Lusztyk, and J.C. Scaiano, J. Am. Chem. Soc., 106, 343 (1984).
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© 1989 Kluwer Academic Publishers
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Chatgilialoglu, C. (1989). Silanes as New Reducing Agents in Organic Synthesis. In: Minisci, F. (eds) Free Radicals in Synthesis and Biology. NATO ASI Series, vol 260. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0897-0_10
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DOI: https://doi.org/10.1007/978-94-009-0897-0_10
Publisher Name: Springer, Dordrecht
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