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An unconventional route to planar graphitic fragments has been demonstrated with the novel synthesis of aromatic polycycles such as 2. The intramolecular Diels–Alder reaction of 1 is followed by aromatization and oxidative aryl–aryl coupling to afford 2 (C30H16) in high yield. The analogous synthesis of a C54H22 polyarene shows that this approach can be used to prepare larger graphitic sections.
Müller et al. (Fri,) studied this question.