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N,N′-Diarylsulfonyl- and N,N′-Dibenzoyl-o-benzoquinone-diimines (4) react remarkably easy with 1,3-diarylbenzo[c]furans (5) to give [π4 + π4] cycloadducts (6). In one case (6a) the chair and boat conformer of this type of adduct could be isolated and the conformations clarified by X-ray crystallography. On heating compounds 6 can rearrange intramolecularly to give 2H-benzimidazoles (7)

zeitschrift für naturforschung b

Cycloadditionen mit o-Benzochinon-diiminen, VI [1].  Reaktionen von Diarylbenzo[c]furanen mit o-Benzochinon-diiminen. Stabile Sessel- und Wannenkonformere in der 5.6.11.12-Tetrahydrodibenzo [b.f] [1.4] diazocinreihe /  Cycloadditions with o-Benzoquinone-diimines, VI [1]. Reactions of 1,3-Diarylbenzo[c]furans with o-Benzoquinone-diimines. Stable Chair and Boat Conformers in the 5,6,11,12-Tetrahydrodibenzo[b,f][1,4]diazocin Series