jo3027752_si_004.cif (26.88 kB)
Twisted Polycyclic Arenes by Intramolecular Scholl Reactions of C3-Symmetric Precursors
dataset
posted on 2013-03-15, 00:00 authored by Anirban Pradhan, Pierre Dechambenoit, Harald Bock, Fabien DurolaWith 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.