Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride

Abstract

2-Styrylcyclopropane-1,1-dicarboxylate treated with anhydrous gallium trichloride undergoes dimerization with the cyclopropane ring opening and the styryl substituent double bond involvement, leading to the formation of polysubstituted cyclic and bicyclic structures with the predominance of the former or the latter depending on the reaction conditions. Most compounds are formed with very high diastereoselectivity. Thirteen major and minor dimeric structures were isolated and reliably characterized, two of which were found to additionally include a chlorine atom. A rare for the reactions of donor-acceptor cyclopropanes example of the formation of a product with the fused cyclobutane ring was effected at–80 °C. Plausible mechanisms of observed processes were discussed.