This thesis is divided into three chapters.
Chapter 1 provides a brief survey of the methodologies currently available for the de
novo synthesis of cyclopentadienes. Particular relevance is given to the more general
methods and to the preparation of structurally interesting compounds. Mechanistic
details will also be given for interesting or unusual reaction pathways.
Chapter 2 presents research findings in the field of the application of the
decarboxylative Claisen rearrangement (dCr) reaction to the synthesis of aromatics. The
development of a novel methodology for the preparation of substituted pyridines will be
described. Firstly, the feasibility of the method will be shown by detailing the
preparation of simple pyridines, carrying alkyl and aryl substituents. Subsequently,
efforts to expand the scope of the methodology will be discussed and attempts to
prepare diversely substituted, chiral and cyclofused compounds detailed. Finally, some
preliminary results concerning the use of the dCr reaction for the synthesis of
cyclopentadienes and cyclopentadienyl anions will be presented.
Chapter 3 provides the experimental details and the characterisation data for all the
compounds synthesised.