C-13 NMR analysis as a useful tool for structural assignment of vinyl- and dienyltin derivatives

Abstract : During the last decade, vinyl- and dienyltin derivatives have been extensively developed and used in organic synthesis. H-1 NMR analysis of these compounds was the first analytical tool employed, together with Sn-119 NMR, for the assignment of the E or Z stereochemistry of vinylstannyl derivatives. In this paper we want to show that C-13 NMR is a powerful tool for structural analysis of vinyl- and dienyltin compounds. Chemical shifts and C-13-Sn119-117 coupling constants are reported for several examples. In all cases described, the (3)J C-13-Sn119-117 values give the most definitive argument for structural assignment. (1)J, (2)J and (3)J C-13-Sn119-117 coupling constants are also reported, along with the alpha, beta, gamma, and delta effects of the stannyl group. When the vinyltin function is functionalized with a heteroatomic substituant, some important changes occur in the chemical shifts and coupling constants. Some examples are given in the alpha-oxygen. -sulfur, -halogen, -silyl, and -tin substituted vinyltin series.
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Submitted on : Monday, March 17, 2014 - 9:54:36 PM
Last modification on : Thursday, February 7, 2019 - 2:44:58 PM

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J.-F. Betzer, P. Le Menez, Joëlle Prunet, J.-D. Brion, J. Ardisson, et al.. C-13 NMR analysis as a useful tool for structural assignment of vinyl- and dienyltin derivatives. SYNLETT, Georg Thieme Verlag, 2002, pp.15/01/2014. ⟨10.1055/s-2002-19316⟩. ⟨hal-00954855⟩

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