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Una reducción quimioselectiva de los alquinos a los (E) -alquenos

Barry M Trost1, Zachary T Ball, Thomas Jöge

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu

Journal of the American Chemical Society
|July 4, 2002
PubMed
Resumen

Este estudio presenta un nuevo método en dos etapas para la transreducción de alquinas a (E) -olefinas. El proceso implica la hidrosilación catalizada por rutenio seguida de la protodisilación, ofreciendo una ruta sintética versátil.

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
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E1 Reaction: Kinetics and Mechanism

Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only in the...
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