Journal of Organic Chemistry p. 4660 - 4666 (1980)
Update date:2022-08-11
Topics:
Mach, Martin H.
Bunnett, Joseph F.
The three trichlorobenzenes fail to participate in the base-catalyzed halogen dance even on treatment with the favorable base/solvent combination potassium tert-butoxide in hexamethylphosphoric triamide.However, 1,2,3,5- and 1,2,4,5-tetrachlorobenzenes undergo disproportionation to penta- and trichlorobenzenes as well as interconversion into each other.Pentachlorobenzene disproportionates to hexa- and tetrachlorobenzenes, but further reactions of C6Cl6 form pentachlorophenol.Substitution reactions to form aryl tert-butyl ethers are observed as side reactions and are believed to occur by the SNAr mechanism.The phenols produced in several reactions apparently result from E2 cleavage of these ethers.These observations are possibly relevant to the mechanism of formation of 2,3,7,8-tetrachlorodibenzo-p-dioxin from 1,2,4,5-tetrachlorobenzene.
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