The reaction of a series of 2,6-dimethylaryl halides with strong base has been investigated. Debromination to give polymethylbenzenes has been found to occur in all the systems studied and varying amounts of higher-boiling products, mainly polymethyl-bibenzyls, have also been obtained. Various mechanisms for these new reactions are discussed and the participation of an unusual triplet carbene intermediate is suggested. The related thermal decomposition of sodium o-halophenates has also been investigated. The participation of a similar carbene intermediate in this reaction appears to be unlikely. Possible mechanisms for the formation of diphenylmethanes obtained in the decomposition of sodium pentachlorophenate in methylbenzenes, are discussed.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:751382 |
| Date | January 1969 |
| Creators | Hall, Julia Kathleen Aylmer |
| Contributors | Cadogan, John Ivan George |
| Publisher | University of St Andrews |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/10023/15017 |
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