Layered Compounds. LXIII. Bromination of Double- and Triple-layered Paracyclophanes

Article abstract of DOI:10.1246/bcsj.53.1677

Triple-layered paracyclophanes underwent bromination to give exclusively monobromo derivatives substituted to the inner benzene.The reactions were markedly accelerated by the transannular electronic interaction as compared to - and double-layered paracyclophanes, and thier enhanced reactivities were demonstrated by some competitive reactions.The relative rates of <2.2> and <3.3> systems are in reverse order for the triple-layered and double-layered series.Their reaction mechanisms were discussed.