Non-IPR Chlorofullerenes Obtained from IPR C ₆₀ by Stone–Wales Rearrangements, ^#1809 C ₆₀ Cl ₁₀ and ^#1806 C ₆₀ Cl ₂₆

Chlorination of isolated pentagon rule (IPR)-fullerene C₆₀ with a SbCl₃/SbCl₅ mixture at 320 °C and pure SbCl₅ at 500 °C promotes Stone-Wales rearrangements leading to non-IPR chlorofullerenes ^#1809C₆₀Cl₁₀ (with ca. 15% yield) and ^#1806C₆₀Cl₂₆ as low-soluble crystalline products. According to single-crystal XRD analysis, the chlorination pattern of <i>C</i>_<i>s</i>-^#1809C₆₀Cl₁₀ with two fused pentagon pairs in the carbon cage contains the addition pattern of known <i>C</i>_2<i>v</i>-^#1809C₆₀X₈ (X = H, Cl) as a substructure. The chlorination pattern of <i>C</i>₂-^#1806C₆₀Cl₂₆ with four pairs of fused pentagons in the carbon cage features the presence of seven- and eight-membered chains of <i>ortho</i> chlorine attachments. The known Cl and CF₃ derivatives of both non-IPR ^#1809C₆₀ and ^#1806C₆₀ carbon cages are compared.