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

J.-F. Betzer (1) , P. Le Menez (2) , Joëlle Prunet (3) , J.-D. Brion (2) , J. Ardisson (1) , A Pancrazi (1)

1 SOSCO - Synthèse Organique Sélective et Chimie Organométallique
2 Laboratoire de Chimie des Substances Naturelles
3 DCSO - Laboratoire de synthèse organique

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.

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, 2002, 1, pp.15/01/2014. ⟨10.1055/s-2002-19316⟩. ⟨hal-00954855⟩