Abstract
Based on primary and β-secondary isotope effects, it is established that the isomerization of epoxides into allylic alcohols catalyzed by supported Au nanoparticles proceeds via an unsymmetrical concerted transition state in which there is partial positive charge developing on the C-O carbon atom progressing C-H abstraction. A carbocationic intermediate can be formed only in cases of sufficient stabilization of the positive charge by appropriate substituents.
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