196-23-6Relevant articles and documents
π-Conjugated benzoperylenes: Sequential C-S bond cleavage and charge distribution patterns of the anions
Benshafrut, Ronnie,Rabinovitz, Mordecai,Hoffman, Roy E.,Ben-Mergui, Naama,Muellen, Klaus,Iyer, Vivekanantan S.
, p. 37 - 48 (2007/10/03)
Chemical reduction of polyaromatic hydrocarbons yielded solutions of long-lived polyanionic species. Reduction of a sulfur heterocycle afforded a stable sulfur-containing dianion. Sulfur extrusion from this dianion proceeded upon further contact with the reducing metal. NMR and UV studies indicate a sulfur extrusion mechanism different than that previously observed in THF. Electron transfer to the already reduced hydrocarbon skeleton results in the stepwise cleavage of the two C-S bonds and the extrusion of a sulfur atom. Dimers of aromatic hydrocarbons such as pyrene and phenanthrene have been reduced as well. The interplay between coulombic repulsions and resonance energies is described.