A Novel Strategy for the Synthesis of ω-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.

Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals: A New Synthesis of 1,1-Difluoro-1-iodo Alditols

“…There are several procedures for the synthesis of difluoroalkyl iodides in the literature. Among those reported are the addition of diiododifluoromethane to olefins 5 and the oxidative decarboxylation of α,α-difluoro carboxylic acids under Hunsdiecker reaction conditions …”