The structure of fullerene compounds

This account reviews fullerene chemistry research at Sussex. C₆₀Ph₂ and C₆₀Ph₄ have been isolated as minor products from the reaction of C₆₀Cl₆ with C₆H₆ and FeCl₃. [70]Fullerene reacts with ICl in C₆H₆ producing a single isomer of C₇₀Cl₁₀ in high yield. C₇₀Ph₈, which has a [5,6] cage double bond that can be selectively functionalized, or C₇₀Ph₁₀ are produced by the electrophilic substitution of C₇₀Cl₁₀ into C₆H₆ in the presence of FeCl₃. C₇₀Ph₉OH is isolated as a minor component of the foregoing reaction mixtures. Autoxidation of C₇₀Ph₈ yields the bislactone, C₇₀Ph₈O₄, which has an eleven atom ring in the surface of the cage. Cycloaddition to the [5,6] double bond of C₇₀Ph₈ with anthracene, C₁₄H₁₀, in C₆H₆ produces C₇₀Ph₈(C₁₄H₁₀). Two new methanofullerenes, C₆₀(CBr₂) and C₆₀(CHCN), are produced by treating [60]fullererie in C₆H₆ with either CH ₂BrCN or CHBr₂ in the presence of LDA. Reaction of [60]fullerene with alkyl buta-2,3-dienoates in the presence of a phosphine results in [3 + 2] cycloadditions which produce alkyl 3'H-1,2-([1',2']cyclopenta)[60]fullerene-5'-carboxylates. [60]Fullerene reacts with Pt(cod)2, producing an insoluble precipitate of PtC₆₀, further reaction with the bidentate ligand, Ph ₂P(CH₂)(n)PPh₂) [n = 2 or 3] in PhMe yields the low solubility complexes Pt(η₂-C₆₀)[Ph₂P(CH₂)(n)PPh₂)] (n = 2 or 3). Mixing of C₆H₆ solutions of [60]fullerene with P₄ or vapour-solid reaction of [60]fullerene with P₄ results in the formation of the intercalate C₆₀(P₄)₂; there is no evidence for significant charge-transfer between the donor (P₄) and acceptor (C₆₀) molecules.