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Updated: May 20, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Epoxidation of olefins with a silica-supported peracid
Rossella Mello1, Ana Alcalde-Aragonés, María Elena González Núñez
1Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Avda. Vicente Andrés Estellés s.n., 46100-Burjassot, Valencia, Spain.
Abstract:
Anhydrous [2-percarboxyethyl] functionalized silica (2a) is an advantageous oxidant for performing the epoxidation of olefins 1. Epoxides 3 do not undergo the ring-opening reactions catalyzed by the acidic silica surface, except for particularly activated cases such as styrene oxide. The hydrophilic and acidic character of the silica surface does not interfere with the directing effects exerted by allylic H-bond acceptor substituents. The alkenes 1 carrying hydroxyl groups react with silica-supported peracid 2a faster than unsubstituted alkenes, thus reversing the trend known for reactions with soluble peracids. These results are attributed to the H-bond interactions of substrate 1 with the silanol and carboxylic acid groups bonded to the silica surface.
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