Journal of fluorine chemistry

Highly selective synthesis of [(perfluoroalkyl) methyl] oxiranes (by the addition of iodoperfluoroalkanes to allyl acetate)

V Církva, B Améduri, B Boutevin, O Paleta

Index: Cirkva, Vladimir; Ameduri, Bruno; Boutevin, Bernard; Paleta, Oldrich Journal of Fluorine Chemistry, 1997 , vol. 83, # 2 p. 151 - 158

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Citation Number: 32

Abstract

Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes RF-I (RF= C4F9, C6F13 C8F17) with allyl acetate, RFCH2CHICH2OAc (1a–1c) and rearranged adducts RFCH2CH (OAc)-CH2I (2a–2c), were converted chemoselectively to the corresponding oxiranes RFCH2CH (-O-) CH2 (3a–3c) in yields of 94–96%(total yields of the two-step synthesis starting from RF-I were 85–87%). The chemoselectivity of the oxirane formation appeared ...