Functionalisation of hydrocarbons using fluorinated alkenes

Abstract

Functionalisation of hydrocarbons is a field of continuing activity and a variety of approaches to this field, have been taken. This thesis is concerned with the functionalisation of the carbon-hydrogen bond, in hydrocarbons, using fluorinated alkenes via a free radical chain mechanism. Addition of the nucleophilic alkyl radical to the electrophilic fluorinated alkene, specifically hexafluoropropene, occurs readily to give incorporation of the polyfluoroalkyl group into a number of hydrocarbons, including aliphatic, mono-, bi- and polycyclic systems. Further chemistry of these polyfluoroalkylated systems has been investigated, including dehydrofluorination of the polyfluoralkyl group to give a series of novel mono- di- and poly-enes with polyfluoroalkenyl groups. Perfluorination of the polyfluoroalkylated systems, using high valency metal fluorides, produced a range of new perfluorocarbons of interest and the monocyclic polyfluoroalkylated systems' were further functionalised, by radical chemistry, to give isomeric products.