Synlett

'Metal Ion Electrophilic Catalysis' in Ring-Opening Reactions of 1, 2-Epoxides by Metal Halides in Ionic Liquids

C Betti, D Landini, A Maia

Index: Betti, Cecilia; Landini, Dario; Maia, Angelamaria Synlett, 2006 , # 9 p. 1335 - 1338

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Citation Number: 9

Abstract

Abstract Metal ion electrophilic catalysis (Li+> Na+>> K+) has been found in ring-opening reactions of 1, 2-epoxides 1-5 by metal halides MHal in ionic liquids. The results have been rationalized on the basis of a transition state where the cation M+ stabilizes the negative charge developing on the oxygen atom of the oxirane ring while favoring the nucleophilic attack at the adjacent carbon by the ion-paired anion Hal-.