The influence of structure on reactivity in alkene metathesis

David J. Nelson, Jonathan M. Percy

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Abstract

Abstract Alkene metathesis has grown from a niche technique to a common component of the synthetic organic chemistry toolbox, driven in part by the development of more active catalyst systems, or those optimized for particular purposes. While the range of synthetic chemistry achieved has been exciting, the effects of structure on reactivity have not always been particularly clear, and rarely quantified. Understanding these relationships is important when designing new catalysts, reactions, and syntheses. Here, we examine what is known about the effect of structure on reactivity from two perspectives: the catalyst, and the substrate. The initiation of the precatalyst determines the rate at which active catalyst enters the catalytic cycle; the rate and selectivity of the alkene metathesis reaction is dependent on how the substrate and active catalyst interact. The tools deployed in modern studies of mechanism and structure/activity relationships in alkene metathesis are discussed.
Original languageEnglish
Title of host publicationAdvances in Physical Organic Chemistry
EditorsIan H. Williams, Nicholas H. Williams
Pages81-188
Number of pages108
Volume48
DOIs
Publication statusPublished - 8 Nov 2014

Publication series

NameAdvances in Physical Organic Chemistry
PublisherAcademic Press

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Keywords

  • organometallic chemistry
  • ruthenium
  • alkene metathesis
  • kinetics
  • organic synthesis

Cite this

Nelson, D. J., & Percy, J. M. (2014). The influence of structure on reactivity in alkene metathesis. In I. H. Williams, & N. H. Williams (Eds.), Advances in Physical Organic Chemistry (Vol. 48, pp. 81-188). (Advances in Physical Organic Chemistry). https://doi.org/10.1016/B978-0-12-800256-8.00002-3