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Title: Applications of lithium compounds in organic synthesis
Author: Hamilton, A. L.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 1998
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The lithiation and subsequent condensation with an electrophile is a useful reaction in many 'total' syntheses. This study was undertaken to investigate the lithiation reactions of several organic molecules. In Chapters 2 and 3, the lithiation of a range of N-pivaloyl-o-toluidines was studied, with the resultant formation of indoles (Chapter 2) and reaction with carbon monoxide to form a carbonylated product (Chapter 3). The lithiation reaction was then applied to 2,5-dimethyl-1,4-phenylene-di-N-pivaloylamine as an attempt to effect quadruple lithiation. However, only double lithiation was observed. In Chapter 4, the attempted lithiation of trifluoroacetylanilines, was studied to see whether it is possible to effect lithiation on the aromatic ring to yield a dianion. Both alkyl and aryllithium reagents were observed to act as nucleophiles towards the substrates, resulting in displacement of the trifluoromethyl group. In Chapters 5, 6 and 7, lithiation of pyridones was investigated. Lithiation and electrophile trapping were found to readily occur for 3-methyl- (Chapter 6) and 6-methyl-2-pyridone (Chapter 5). However, the research on 4-methyl-2-pyridone (Chapter 6) showed that n-butyllithium caused either (i) lithiation at the 4-position in the ring or (ii) acted as a nucleophile, with the addition of a butyl group at the 6-position in the ring. The reaction of n-butyllithium and 3-cyano-6-methyl-2-pyridone was studied (Chapter 7). n-Butyllithium was found to act as a nucleophile towards 3-cyano-6-methyl-2-pyridone, resulting in the addition of a butyl group.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available