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Isomerization During Olefin Metathesis: An Assessment of Potential Catalyst Culprits

Authors

  • Carolyn S. Higman,

    1. Department of Chemistry and Centre for Catalysis Research & Innovation, University of Ottawa, Ottawa, ON, K1N 6N5 (Canada)
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  • Lucie Plais,

    1. Department of Chemistry and Centre for Catalysis Research & Innovation, University of Ottawa, Ottawa, ON, K1N 6N5 (Canada)
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  • Prof. Deryn E. Fogg

    Corresponding author
    1. Department of Chemistry and Centre for Catalysis Research & Innovation, University of Ottawa, Ottawa, ON, K1N 6N5 (Canada)
    • Department of Chemistry and Centre for Catalysis Research & Innovation, University of Ottawa, Ottawa, ON, K1N 6N5 (Canada)

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Abstract

Two ruthenium hydride complexes commonly proposed as agents of unintended isomerization during olefin metathesis are examined for their activity in isomerization of estragole, a representative allylbenzene. Neither proves kinetically competent to account for the levels of isomerization observed during cross-metathesis of estragole by the second-generation Grubbs catalyst. A structure–activity analysis of selected ruthenium hydride complexes indicates that higher isomerization activity correlates with a more electrophilic metal center.

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