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Mechanistic Insights into the Very Efficient [ReO3OSiR3]-Catalyzed Isomerization of Allyl Alcohols

Authors

  • Stéphane Bellemin-Laponnaz,

    1. Laboratoire de Chimie des Métaux de Transition et de Catalyse, Université Louis Pasteur, Institut le Bel, URA 424 CNRS, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex (France), Fax: Int. code +388416171, e-mail: osborn@chimie.u-strasbg.fr
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  • Dr. Hervé Gisie,

    1. Laboratoire de Chimie des Métaux de Transition et de Catalyse, Université Louis Pasteur, Institut le Bel, URA 424 CNRS, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex (France), Fax: Int. code +388416171, e-mail: osborn@chimie.u-strasbg.fr
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  • Dr. Jean Pierre Le Ny,

    1. Laboratoire de Chimie des Métaux de Transition et de Catalyse, Université Louis Pasteur, Institut le Bel, URA 424 CNRS, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex (France), Fax: Int. code +388416171, e-mail: osborn@chimie.u-strasbg.fr
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  • Prof. John A. Osborn

    Corresponding author
    1. Laboratoire de Chimie des Métaux de Transition et de Catalyse, Université Louis Pasteur, Institut le Bel, URA 424 CNRS, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex (France), Fax: Int. code +388416171, e-mail: osborn@chimie.u-strasbg.fr
    • Laboratoire de Chimie des Métaux de Transition et de Catalyse, Université Louis Pasteur, Institut Le Bel, URA 424 CNRS, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex (France), Fax: Int. code +388416171, e-mail: osborn@chimie.u-strasbg.fr
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  • Dedicated to the late Geoffrey Wilkinson, mentor, inspirer, and friend

Abstract

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The catalytic isomerization of allyl alcohols by a 1,3-OH shift can be carried out very rapidly in the presence of [ReO3OSiR3] catalysts at 25°C or below [Eq. (a)]. Kinetic studies suggest that the rearrangement takes place via a cyclic transition state involving a Re = O group. R = Me, Ph.

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