Completely Regioselective, Highly Stereoselective Syntheses of cis-Bisfullerene60 Adducts of 6,13- Disubstituted Pentacenes

摘要

We have been interested in the Diels-Alder chemistry between C_(60) and large linear acenes like pentacene for several years. Our initial studies indicated that 1 equivalent of C_(60) cycloadds across the central 6,13- carbons of pentacene in refluxing toluene to yield the C_(2v) symmetric monoadduct 1 in 59% uncorrected yield. Utilizing a 10-fold excess of C_(60) pushes the yield of monoadduct 1 to 86% based upon pentacene consumed.