Preparation of polymer-supported peroxy-acids and their use to oxidise olefins to epoxides

Abstract

Treatment of carboxy-substituted polystyrene resins with hydrogen peroxide in methanesulphonic acid gave resins containing aromatic peroxy-acid residues (3.5–4.0 mmol g^–1). The resins generally reacted with di- and tri-substituted olefins in tetrahydrofuran at 40 °C to give epoxides (or products derived from epoxides) in yields greater than 50%. Monosubstituted olefins reacted poorly. In cases where mixtures of stereoisomeric epoxides were formed the proportions of the isomers were essentially the same as those obtained by using monomeric aromatic peroxy-acid reagents.