Electrophilic fluorination at saturated carbon

Abstract

Chapter 1 - Chapter 1 contains a discussion of the preparation and properties of elemental fluorine. A review of the use of elemental fluorine as a selective fluorinating in organic chemistry is given and the preparation and use of other selective fluorinating agents is also described. Chapter 2 - Direct fluorination methodology for the preparation of selectively fluorinated hydrocarbon compounds was developed and used to prepare a range of both cyclic and acyclic fluoroalkanes. Selectfluor™ a commercial fluorinating agent of the N-F class, was also used to prepare selectively fluorinated hydrocarbon compounds and the results of these experiments were used to gain information about the mechanism of the corresponding direct fluorination reactions. It was concluded that the direct fluorination reactions proceed via an aliphatic electrophilic substitution mechanism. Chapter 3 - An amidation procedure which involves the use of elemental fluorine, boron trifluoride and acetonitrile was developed and used to prepare various selectively amidated hydrocarbon derivatives. Chapter 4 - The selective direct fluorination of alkyl chains which are attached to an electron withdrawing group (EWG) was investigated to establish the effect that the EWG has on the fluorination reaction. For comparison, substrates were also reacted with Selectfluor™. Chapter 5 - Chapter 5 is concerned with the preparation of selectively fluorinated N-containing heteroaromatic compounds using fluorine-iodine mixtures. Chapters 6-9 - Experimental details of the work discussed in Chapters 2-5.