Reactive intermediates in the reactions of aryl halides with bases
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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.
Thesis, PhD Doctor of Philosophy
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