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The cycloaddition of the bisdienophile 1 and the benzo[c]furan generated in situ from the precursor 2 yielded the nonaphene derivative 4 (Scheme 1). A related reaction (Scheme 3) was used for the preparation of the dithianonaphene systems 6a, b, c, namely the [2π+8π] cycloaddition of 1 and 2H-benzothiete (5/5′). Acidic dehydration (aromatization) of 6a, b, c led to the dithianonaphenes 7a, b, c (Scheme 4).

zeitschrift für naturforschung b

Aufbau von Nonaphen-und Dithianonaphen-Derivaten - Modellverbindungen für gewinkelte Bandstrukturen / Generation of Nonaphene and Dithianonaphene Derivatives - Model Compounds for Bent Molecular Ribbons