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Title: De novo synthesis of highly substituted pyridines
Author: Paina, Federica
ISNI:       0000 0000 7175 8362
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2008
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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.
Supervisor: Craig, Donald Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral