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The Physical Origin of Saytzeff’s Rule

Benoı̂t Braı̈daUPMC Université Paris 06, CNRS UMR 7616, Laboratoire de Chimie Théorique, Case Courrier 137, 4 Place Jussieu, 75252 Paris, France. [email protected]Vinca PranaUPMC Université Paris 06, CNRS UMR 7616, Laboratoire de Chimie Théorique, Case Courrier 137, 4 Place Jussieu, 75252 Paris (France),Philippe C. HibertyUniversité de Paris‐Sud, CNRS UMR 8000, Laboratoire de Chimie Physique, 91405 Orsay Cédex (France), Fax: (+33) 1‐6915‐4447
2009en
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Hyperconjugation, hybridization, or what? The hyperconjugative effects in primary, secondary, and tertiary alkenes were estimated using ab initio valence bond methods to trace the origin of the empirical Saytzeff rule, which states that the formation of the more substituted alkene is preferred. Hyperconjugation between the π bond and the π-donating substituents governs Saytzeff's rule, whereas all other factors support an anti-Saytzeff pathway.

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