Diels-alder reactivity of polycyclic aromatic hydrocarbon bay regions: implications for metal-free growth of single-chirality carbon nanotubes

A clean diels-alder reaction between bisanthene and diethyl acetylenedicarboxylate in presence of hot toluene to yield a rearomatized 1:1 cycloadduct and a rearomatized 2:1 cycloadduct is reported. A Diels-Alder cycloaddition/rearomatization strategy in presence of acetylene or a 'masked acetylene' as the dienophile could be used to grow single-chirality carbon nanotubes from suitable hydrocarbon templates, without metal catalysis.