Scheme 59.

Cycloaddition of in situ generated arynes to the 7,14-di-mesityl-bisanthene, i.e., 7,14-dimesitylphenanthro[1,10,9,8-opqra]perylene [205]. Reagents and conditions: (a) 3-amino-2-naphthoic acid, isoamyl nitrite, PhMe, rfx, 1 h, Y = 39%; (b) 1-bromonaphthalene, NaNH₂, THF, rfx, 2 h, Y = 49%;(c) 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, CsF, THF, rfx, 1 d, Y = 72% or anthranilic acid, isopentyl nitrite, PhMe, 1 h, Y = 75%; (d) n-BuLi, 1,2,4,5-tetrabromobenzene, PhMe, rfx, 1.5 h, Y = 51%; and (e) 9-bromophenanthrene, NaNH₂, THF, rfx, 12 h, Y = 40%.