Ein hochsymmetrisches Produkt einer sechsfachen [4 + 2]‐Cycloaddition des C₆₀‐Fullerens

Spherical Aromaticity of Fullerenes

“…Successive 6-fold additions of transition-metal fragements, 159 malonates, 24,125,137,[160][161][162][163][164][165][166] dienes, 167 or azomethine ylids 168 were used to synthesize T h -symmetrical hexakisadducts whose general structure is represented in Figure 10. The inherent aesthetically pleasing structural motif is unique in organic chemistry.…”

Cycloaddition Reactions of Butadiene and 1,3‐Dipoles to Curved Arenes, Fullerenes, and Nanotubes: Theoretical Evaluation of the Role of Distortion Energies on Activation Barriers

“…[5,21,31,32] The [4+2] Diels-Alder reaction involving fullerenes takes place readily due to the electron-deficient nature (low LUMO) of C 60 . A wide variety of dienes were found to react with C 60 , [33][34][35][36][37][38] but some of the final cycloaddition adducts were shown to undergo the retro-Diels-Alder reaction. [8] Success was also achieved for the addition of dienes such as ortho-quinodimethane due to the final gain in aromaticity of the cycloaddition product.…”

Molecular self-healing mechanisms between C60-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy

“…3 Other good dienophile candidates for reversible [4+2] cycloadditions are fullerenes. [25][26][27][28] Schwenninger et al used the reversibility of the Diels-Alder reaction to synthesize symmetric equatorial tetra adducts of C 60 with labile bound anthracene molecules as directing protection groups. Since its discovery 18 C 60 has shown to undergo a large number of different chemical reactions [19][20][21][22][23][24] where the [4+2] cycloaddition is of particular interest.…”