The [4 + 2] cycloaddition of anthracene with C60F18; anthracene goes ring walking

摘要: From the [4 + 2] cycloaddition of anthracene at curved face C60F18 we have isolated two main isomers Cs and C1 symmetry (isomers 1 2, respectively) in ca. 3 ∶ 2 relative yields; isomer 2 contained traces a third isomer, also symmetry. Of four mono adducts that can, principle, be formed by this cycloaddition, yields three obtained reflect differences steric hindrance between fluorine aromatic addends. The major (1) is reasonably stable, but more crowded (2) reverts readily to on standing, undergoes rearrangement (1). This first example spontaneous migration cycloaddend from one 6 ∶ 6-bond another same fullerene cage surface. UV/VIS spectrum significantly different for C60F18, suggesting some electronic interaction may exist addend cage. Anthraquinone produced as by-product reaction (and either C60 or C60Cl6 anthracene) showing acts here an oxidant.