The influence of structure on reactivity in alkene metathesis

Nelson, David J. and Percy, Jonathan M. (2014) The influence of structure on reactivity in alkene metathesis. In: Advances in Physical Organic Chemistry. Advances in Physical Organic Chemistry, 48 . Academic Press, pp. 81-188. ISBN 978-0-12-800256-8

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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.