The thermolysis and photolysis of a number of cyclic sulphones has been studied, with a view to developing these reactions as possible synthetic processes. Some substituted dihydronaphthothiophene sulphones were prepared and those containing a pent-4-ene sidechain successfully underwent intramolecular Diels-Alder cyclisations. 2-Phenylthietan was prepared by a new route and the preparation and pyrolysis of some 2-phenylthietan 1,1-dioxide derivatives was studied. Some 2-(alkan-1-o1) 3,3-dimethylthietan sulphones were prepared and the dehydration of these, with a view to preparing alk-1-ene derivatives, was studied. Phosphorus oxychloride in pyridine was the most successful of those reagents tried. The alk-1-ene derivatives were shown to have unusual thermal behaviour, when they ring-expanded to their respective sultines under flash vacuum thermolysis conditions. The use of 3,3-dimethylthietan 1,1-dioxide as a starting material for a new route to chrysanthemates has been studied. Methyl-trans-chrysanthemate was eventually identified as one of the products after a 4-step synthesis from this sulphone. A number of cyclic sulphides were prepared using phase transfer catalysis.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:350742 |
| Date | January 1984 |
| Creators | Clarke, Stephen G. |
| Publisher | University of Leicester |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/2381/34056 |
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