Studies in aryne chemistry

The principal methods for the generation of arynes and the types of reactions which they undergo are briefly reviewed. Tetrachlorobenzyne has been generated from pentachlorophenyl magnesium chloride, pentachlorophenyl lithium, and tetrachloroanthranilic acid. Reactions of tetrachlorobenzyne with benzene, substituted benzenes, naphthalene, anthracene, furan, tetraphenylcyclopentadienone, 1,3-diphenyl-isobenzofuran, crotonaldehyde and acrolein are reported. Cycloadducts are obtained from those reactions in good yield. Certain reactions of tetrachlor-4-pyridyl lithium are reported. [Continues.]