Journal of fluorine chemistry

Chemistry of [(perfluoroalkyl) methyl] oxiranes. Regioselectivity of ring opening with O-nucleophiles and the preparation of amphiphilic monomers

V Cı́rkva, B Améduri, B Boutevin, O Paleta

Index: Cirkva, Vladimir; Ameduri, Bruno; Boutevin, Bernard; Paleta, Oldrich Journal of Fluorine Chemistry, 1997 , vol. 84, # 1 p. 53 - 61

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Citation Number: 21

Abstract

The reactions of oxiranes RFCH2CH (–O–) CH2 (RF≡ C4F9, C6F13, C8F17; 4a–4c) with a series of alkanols in the presence of a Lewis acid took place at the terminal carbon atom with complete regioselectivity. 2-Hydroxyethyl methacrylate and acrylate reacted similarly. The reaction with alkane diols was controlled to proceed with one or two molecules of the oxiranes chemoselectively. Non-regioselective, base-catalysed ring opening by ...