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Abstract
The Schiff bases 4-([2.2]paracyclophanylidine)-4-methyl-aniline (1), p-tolylidine-4[2.2]-paracyclophanylamine (5) and pipe-ronylidine-4[2.2]paracyclophanylamine (7) have been reacted with benzyne (2) to afford fused paracyclophenanthridinophane derivatives 3, 6, and 8, respectively. (4-[2.2]-Paracyclophanylidine) cyclohexylamine (9) reacted with three equivalents of benzyne; two undergoing ene-addition and one [4 + 2]cycloaddition to afford compound 10.