Synthesis of (E,E)- and (Z,Z)-1,5-Cycloalkadienes by Means of the Electrochemical Cyclization of Allylic 1,ω-Dibromides

Article abstract of DOI:10.1246/bcsj.60.2429

Electrolysis of (E,E)-1,n-dibromo-2,(n-2)-alkadienes (n=12, 14) in tetrahydrofuran gave the corresponding twelve or fourteen-membered (E,E)-1,5-cycloalkadienes, albeit in low yields, together with (E)-4-vinylcycloalkenes and isomeric alkadienes.Similar electrolysis of (Z,Z)-1,n-dibromo-2,(n-2)-alkadienes (n=10, 12, 14) gave the corresponding ten, twelve, or fourteen-membered (Z,Z)-1,5-cycloalkadienes in 11 to 13percent yields, with the accompanying formation of (Z)-4-vinylcycloalkenes and isomeric alkadienes.