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Title: Electrocyclisation as a route to tricyclic azepine systems
Author: Reece, Donald H.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1992
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This research was concerned with the synthesis and reactions of nitrile ylides conjugated with two aromatic rings, of which one was a heteroaromatic ring and the other was a benzene ring. After the nitrile ylides were prepared they reacted exclusively via 1,7-electrocyclisation to form azepines with two fused rings. The reactions demonstrated a high level of periselectivity in thiophene, but a much lower preference in pyridine. No difference in reactivity was observed in the cyclisation on to electron rich or poor rings, both gave high yields of products. This research has also developed a new general synthesis of the amide precursors for nitrile ylides by the use of the novel boronic acid 2-N-benzoylaminomethylphenylboronic acid. Further research was also undertaken to develop another route to the amide precursors to the nitrile ylide via a scheme which requires the cycloaddition of a 1,3-dipole on to a functionalised alkyne.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available