Journal of Fluorine Chemistry

Fluorinated epoxides: 5. Highly selective synthesis of diepoxides from α, ω-diiodoperfluoroalkanes. Regioselectivity of nucleophilic epoxide-ring opening and new …

V Cı́rkva, M Gaboyard, O Paleta

Index: Cirkva, Vladimir; Gaboyard, Manuel; Paleta, Oldrich Journal of Fluorine Chemistry, 2000 , vol. 102, # 1-2 p. 349 - 361

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Citation Number: 12

Abstract

An improved procedure for the radical addition of α, ω-diiodoperfluoroalkanes I–(CF2CF2) n– I (n= 2, 3) to allyl acetate that afford the corresponding bis-adducts AcOCH2CHICH2 (CF2CF2) nCH2CHI–CH2OAc (2a–2b) has been developed. The primary bis-adducts 2a– 2b suffered a subsequent rearrangement in the addition mixture to afford semi-rearranged adducts AcOCH2CHICH2–(CF2CF2) n–CH2CH–(OAc) CH2I (3a–3b) in an amount of ca. ...