An Improved Method for the Regiospecific Synthesis of Polysubstituted [2.2]Paracyclophanes

4,16-Disubstituted, 4,7,12,15-tetrasubstituted, 4,8,12,16-tetrasubstituted and 4,5,7,8,12,13,15,16-octasubstituted [2.2]paracyclophanes can be prepared in significantly improved yields and excellent regiospecificities via the Winberg 1,6elimination-dimerization reaction from substituted (4-methylbenzyl)trimethylammonium hydroxides. Using 2-chlorophenothiazine instead of phenothiazine as a polymerization inhibitor results in a doubling of product yields.