Elemental fluorine as a valid synthetic reagent

Abstract

Chapter I Chapter I reviews the uses of elemental fluorine in selective organic synthesis and its use in the generation of selective electrophilic fluorinating agents. Chapter II Chapter II describes a systematic investigation into suitable solvents for the direct fluorination of deactivated aromatic systems. After highlighting 98% formic acid and 98 % sulphuric acid as excellent media for fluorinations, a number of other protonic acids were investigated. The work confirms the power of the resulting in situ fluorinating species is dependent on the pKa of the protonic acid. Chapter III Chapter III describes the use of elemental fluorine, in combination with strong acids, for the generation of powerful electrophilic halogenating agents derived for iodine, bromine and some interhalogens. The use of iodoaromatics in the incorporation of perfluoroalkyl groups into aromatics is also detailed. Chapter IV Chapter IV describes the use of elemental fluorine, in combination with iodine, for the direct fluorination of pyridines and quinoline in the 2- position. The use of elemental fluorine and an alcohol in the 2-alkoxylation of pyridine is also described. Investigation into a number of other potential nucleophiles for the 2- functionalisation of pyridines is also detailed. Chapter V-VII Experimental details relating to Chapters II-IV. Appendix One-Three Relevant (^1)H nmr, (^13)C nmr, (^19)Fnmr / IR data and mass spectra data.