Synthesis and Reactions of 2-(4'-Methoxyphenyl)-4-Aryl-1 :3-Butadienes

Department of Chemistry, Ramnarain Ruia College, Bombay-19

Received 22 September 1971; revised M S S received 3 July 1972

Condensation of diethyl-3-(4'-methoxyphenyl) glutaconate (I) with various aromatic aldehydes furnished a series of 3-(4'-methoxyphenyl)-4-(substituted benzylidene) glutaconic acids (II), which upon thermal decarboxylation formed corresponding 2-(4'-methoxyphenyl)-4-aryl-1 : 3-butadienes (Ill). Application of Diels-Alder reaction to (Ill) gave 3-aryl-5-(4'-methoxyphenyl)-1 :2 : 3 : 6-tetrahydrophthalic anhydrides (IV), while bromination of (Ill) yielded dibromides of the type (V).