Polyhalogeno-aromatic compounds. Part VIII. Reactions of hexabromobenzene with nucleophiles

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690002337

Abstract

Hexabromobenzene unlike its chloro- or fluro-analogues undergoes protodebromination when treated with sodium methoxide in methanol and ethyl methyl ketone to give a mixture of tetrabromobenzenes. With piperidine or ethanolic ammonia debromination and some nucleophilic substitution occurs. Hydrazine gives only 1,2,3,4-tetrabromobenzene while cyclohexyamine or sodium methoxide in pyridine give the corresponding substitution products. Attempts have been made to rationalise these result.

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