Hexafluoropropene oxide oligomers

Hexadiene-3-ol, hydrogenation, 30 361 Hexadiene, reaction with HCN, 33 19-20 Hexafluoropropene oxide oligomers, 42 497 Hexahydronaphthalenes, intermediates of naphthalene hydrogenation, 18 32, 33... 

Fluorinated epoxides are very important synthetically. Perfluoroalkenes can be oxidized by numerous means to the corresponding epoxides. The most commonly encormtered epoxide is hexafluoropropene oxide (HFPO), which is made from hexafluoropropene and is used in the synthesis of oligomers and as a source of difluorocarbene. HFPO is a colorless, nonflammable gas, boiling at -27.4 °C it can be ring-opened easily by nncleophiles or electrophiles imder a variety of conditions. HFPO can be rearranged by flnoride ion to perfluoropropionyl flnoride and by Lewis acids snch as UO2 to hexafluoroacetone (HFA). Nncleophiles typically attack the most substituted carbon of the epoxide, freeing the oxyanion to lose fluoride or act as a nucleophile itself Some examples of HFPO reactivity are shown in Scheme 3. 

Anionic fluorinated surfactants containing an oligo(hexafluoropropene oxide) chain have been prepared by anionic oligomerization of hexafluoropropene oxide (HFPO) [98,99] and hydrolysis of the oligomer, an acid fluoride [100] ... 

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