The reactions of the tetrahalogenobenzynes with bicyclo[2,2,1]heptene and bicyclo[2,2,1]heptadiene lead to the formation of cycloadducts. In the latter reactions products derived by (2 + 2)π and (2 + 2 + 2)π cycloadditions are obtained. The ratios of the two adducts are similar to those obtained with other arynes, except in the reactions involving tetrafluorobenzyne.
H. Heaney, J. M. Jablonski, K. G. Mason and J. M. Sketchley, J. Chem. Soc. C, 1971, 3129 DOI: 10.1039/J39710003129
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