2865-19-2Relevant articles and documents
Stereochemistry of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes
Jousseaume, Bernard,Noiret, Nicolas,Pereyre, Michel,Francès, Jean-Marc,Pétraud, Michel
, p. 3910 - 3914 (2008/10/08)
The stereochemical study of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes revealed an anti β-elimination of (acyloxy)triorganostannanes. The process is highly stereospecific and not perturbed by the presence of a possible internal chelation favoring syn elimination. It corresponds to an open transition state. Kinetics of β-elimination in cyclohexyl and norbornyl systems showed that the reaction is much more rapid with a 180° dihedral angle between the metal and the ester group than with a 60° angle between the two. Stabilization of the partial positive charge developed during the transition state occurs mainly through hyperconjugation effect.