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Twisted Polycyclic Arenes by Intramolecular Scholl Reactions of C3-Symmetric Precursors

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posted on 15.03.2013, 00:00 authored by Anirban Pradhan, Pierre Dechambenoit, Harald Bock, Fabien Durola
With the aim of opening an efficient access to large and sterically crowded polycyclic arenes as well as improving insight into the geometrical preferences of the Scholl reaction, a versatile synthesis strategy has been developed to form a family of flexible yet strongly crowded substrates for multiple dehydrocyclizations. Their intramolecular Scholl reactions lead with high selectivity either to considerably twisted species where the initial C3 symmetry is maintained, or to strongly rearranged products where the formation of multiple [6]­helicene fragments is avoided by the formation of unusual hexa[7]­circulene moieties under loss of the C3 symmetry.