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  • Regioselectivity  (1)
  • Side-chain modifications  (1)
  • 1
    ISSN: 0947-3440
    Keywords: Fullerenes ; Regioselectivity ; Bond labeling ; Methanofullerenes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A computational (AM1) analysis is presented which shows that the observed regioselectivities of multiple cyclopropanations of C60 are due to orbital-allowed processes. Next to the coefficients of frontier orbitals the characteristic cage distortions of the oligomethanofullerenes are discussed. For further experimental corroboration the synthesis and characterization of an unsymmetrical trisadduct with a I, eI, III*-addition pattern are described. Moreover, since a systematic and descriptive assignment of addition patterns in derivatives of C60 and higher fullerenes becomes more and more important, a simple and general algorithm is introduced, which enables unambiguous bond labeling of both [6,6]- and [5,6]-bonds as well as the assignment of the absolute configuration of any fullerene derivative.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0947-3440
    Keywords: Fullerenes ; Active ester ; Coupling reactions ; Side-chain modifications ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Side-chain modifications of fullerenes can be achieved starting from the malonic acid 2, which is easily accessible by saponification of the corresponding diethyl malonate adduct 1 and is therefore an ideal building block for side chain chemistry on fullerenes. Coupling reactions are carried out via the synthesis of the fullerene active ester 4, which is formed by the reaction of the malonic acid 2 with N-hydroxysuccinimide. During this reaction the malonic acid undergoes decarboxylation, yielding an acetic acid derivative instead of a malonic system. The active ester 4 is isolable and represents an ideal building block for fullerene chemistry. Sidechain modifications can also be carried out as one-step reactions by preparing 4 in situ. We have performed coupling reactions with various compounds containing primary or secondary amino groups.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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