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Epoxidation of Olefins with a Silica-Supported Peracid

Rossella Mello, Ana Alcalde-Aragonés, María Elena González Núñez* and Gregorio Asensio

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Avda. Vicente Andrés Estellés s.n., 46100-Burjassot, Valencia, Spain, Email: elena.gonzalezuv.es

R. Mello, A. Alcalde-Aragonés, M. E. González Núñez, G. Asensio, J. Org. Chem., 2012, 77, 6409-6413.

DOI: 10.1021/jo300533b (free Supporting Information)


Abstract

Anhydrous [2-percarboxyethyl] functionalized silica is an advantageous oxidant for epoxidation of olefins. The acidic silica surface does not catalyze ring-opening reactions except for particularly activated styrene oxide. Alkenes carrying hydroxyl groups react with silica-supported peracid faster than unsubstituted alkenes. Products can be isolated after simple filtration and solvent evaporation.

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Key Words

Epoxidation, Prilezhaev Reaction, Peracids


ID: J42-Y2012-2430