The influence of structure on reactivity in alkene metathesis

David J. Nelson, Jonathan M. Percy

Research output: Chapter in Book/Report/Conference proceedingOther chapter contribution

3 Citations (Scopus)

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.
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

Fingerprint

Alkenes
Catalysts
Substrates

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
Nelson, David J. ; Percy, Jonathan M. / The influence of structure on reactivity in alkene metathesis. Advances in Physical Organic Chemistry. editor / Ian H. Williams ; Nicholas H. Williams. Vol. 48 2014. pp. 81-188 (Advances in Physical Organic Chemistry).
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Nelson, DJ & Percy, JM 2014, The influence of structure on reactivity in alkene metathesis. in IH Williams & NH Williams (eds), Advances in Physical Organic Chemistry. vol. 48, Advances in Physical Organic Chemistry, pp. 81-188. https://doi.org/10.1016/B978-0-12-800256-8.00002-3

The influence of structure on reactivity in alkene metathesis. / Nelson, David J.; Percy, Jonathan M.

Advances in Physical Organic Chemistry. ed. / Ian H. Williams; Nicholas H. Williams. Vol. 48 2014. p. 81-188 (Advances in Physical Organic Chemistry).

Research output: Chapter in Book/Report/Conference proceedingOther chapter contribution

TY - CHAP

T1 - The influence of structure on reactivity in alkene metathesis

AU - Nelson, David J.

AU - Percy, Jonathan M.

PY - 2014/11/8

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N2 - 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.

AB - 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.

KW - organometallic chemistry

KW - ruthenium

KW - alkene metathesis

KW - kinetics

KW - organic synthesis

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DO - 10.1016/B978-0-12-800256-8.00002-3

M3 - Other chapter contribution

SN - 978-0-12-800256-8

VL - 48

T3 - Advances in Physical Organic Chemistry

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BT - Advances in Physical Organic Chemistry

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Nelson DJ, Percy JM. The influence of structure on reactivity in alkene metathesis. In Williams IH, Williams NH, editors, Advances in Physical Organic Chemistry. Vol. 48. 2014. p. 81-188. (Advances in Physical Organic Chemistry). https://doi.org/10.1016/B978-0-12-800256-8.00002-3