Preparation of calix[8]arene derivatives functionalized at a single methylene bridge

A calix[8]arene derivative substituted at the single methylene bridge by a chlorine atom reacts at the substituted bridge with O, N, and C nucleophiles under S_N1 conditions. Thiscalix[8]arene can serve as a useful starting material for the preparation of calix[8]arene derivatives functionalized at a single methylene bridge. A large number of calix[8]arenes substituted at a single methylene group can be easily prepared by the reaction (under S_N1 conditions) of a chlorocalix[8]arene derivative with nucleophiles (including aromatic rings and active methylene compounds).