THE ANIONIC ALKYLATION OF EASILY REDUCIBLE ARENES. A PHOTOCHEMICAL ROUTE TO NUCLEOPHILIC AROMATIC SUBSTITUTION OF ANTHRACENE BY ORGANOLITHIUMS

Article abstract of DOI:10.1016/S0022-328X(00)95252-5

High yield nuclophilic addition ensues upon mixing tetrahydrofuran solutions of benzyllithium or cyclooctadienyllithium and anthracene at low temperatures.At least part of this addition proceeds by a single electron transfer pathway.Photolysis of the resulting adducts leads to the elimination of lithium hydride, giving net nucleophilic substitution in approximately 50percent yield.The analogous reaction fails with naphthalene, where photolysis of the organolithium/arene mixture leads to dimeric products derived from the organolithium.