α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:
C6H4(CH3)2 + 4 Br2 → C6H4(CHBr2)2 + 4 HBr Reaction of α,α,α',α'-tetrabromo-o-xylene with sodium iodide affords α,α'-dibromo-o-xylylene, which can be trapped with dienophiles to give naphthylene. In the absence of trapping agents, the xylylene relaxes to α,α'-dibromobenzocyclobutane:
C6H4(CHBr2)2 + 2 NaI → C6H4(=CHBr)2 + 2 NaBr + I2 C6H4(=CHBr)2 → C6H4(CHBr)2 Cycloadditions of these xylylenes provides a pathway to acenes.
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