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Title: Novel methodologies for the synthesis of highly substituted aromatic rings : the development of a microwave mediated approach
Author: Padgham, Alex
ISNI:       0000 0004 7229 4706
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2018
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An interesting transformation involving palladium was recently discovered by the Parsons group, which entailed the cyclisation and fragmentation of furan starting materials to afford highly substituted benzene compounds. The early aim of the project was to investigate the presence of intermediates in the reaction mixture, in an attempt to determine a possible mechanistic pathway. These results laid the foundation for future research; it was subsequently postulated that a similar reaction could be achieved under purely thermal conditions. Investigations led to the discovery that microwave irradiation could successfully initiate the thermal cyclisation of the designed precursors, resulting in moderate to good yields of highly substituted benzene products. Further studies found that, by replacing the terminal alkyne with a nitrile group, a highly substituted pyridine compound could be isolated, and other analogues were investigated, though ultimately unsuccessful. During investigations of the scope of the cyclisation, it was also found that the same conditions could thermally cyclise diyne compounds into furan products: a tricyclic furan was formed from a diyne ether furan precursor, and simple diynes were cyclised into aromatic products and simple bicycles.
Supervisor: Parsons, Philip Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral