title: A novel strategy for the synthesis of omega-functionalized perfluoroalkyl iodides.
abstract: [reaction: see text] The applicability of telomeric alcohols, H(CF(2)CF(2))(n)()CH(2)OH, for the synthesis of omega-functionalized F-alkylating reagents, I(CF(2)CF(2))(n-1)CH(2)OAc (6, n = 5), is demonstrated. The key steps of this optimized method are the "activation" of the HCF(2)- terminus in a lithiation process yielding olefin 2 [(Z+E)-BuCF=CF(CF(2)CF(2))(4)CH(2)OH, 86%] and a successive ozonation reaction in trifluoroethanol media affording ester 3b [CF(3)CH(2)O(2)C(CF(2)CF(2))(4)CH(2)OH, 93%]. Highly stereospecific ozone cleavage of the (E)-2 isomer was observed in methanol due to the competitive oxidation of the solvent.
authors.affiliation: Department of Organic Chemistry, Eötvös Loránd University, P.O. Box 32, H-1518 Budapest 112, Hungary.
authors.forename: Z
authors.initials: Z
authors.lastname: Szlávik
authors.forename: G
authors.initials: G
authors.lastname: Tárkányi
authors.forename: Z
authors.initials: Z
authors.lastname: Skribanek
authors.forename: E
authors.initials: E
authors.lastname: Vass
authors.forename: J
authors.initials: J
authors.lastname: Rábai