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Title: Thermodynamically controlled cyclisation reactions with phenylsulfanyl participation
Author: Carlisle, J.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2003
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Treatment of b-phenylsulfanyl alcohols with acid results in the formation of episulfonium ions. These can be trapped intramolecularly to produce heterocycles. These reactions are under thermodynamic control. This thesis describes the synthesis and subsequent cyclisation of tetrols. In this case there is competition between two episulfonium ions and between two possible secondary hydroxyl nucleophiles. The cyclisation of compounds in which two episulfonium ions can form at the same centre, is also investigated. Finally, the interaction between the ring size (5-vs 6-membered) and sulfur atom position (bound to a tertiary vs a secondary centre) as product-determining factors in competitive cyclisations is explored using diols.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available