Benzyne adds across a closed 5-6 ring fusion in C70: Evidence for bond delocalization in fullerenes

Mark S. Meier, Guan Wu Wang, Robert C. Haddon, Carolyn Pratt Brock, Michael A. Lloyd, John P. Selegue

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

Addition of benzyne to C70 results in four isomeric monoadducts (compounds 1a-d) in a 42:35:13:10 ratio as determined by 1H NMR. These compounds were separated by repeated passes through HPLC columns. The major isomer (1a) resulted from addition to the highly pyramidalized C1-C2 bond as shown by 13C NMR and UV/vis spectroscopy. The structure of the C1-C2 adduct (1a) was confirmed by X-ray crystallography. The second isomer (1b) was assigned as an adduct to the C5-C6 bond on the basis of 13C NMR and UV/vis spectroscopy. Compound 1c exhibited a 13C spectrum consistent with an adduct to the C7 and C8 positions. The presence of sp3 13C NMR resonances proved that the C7-C8 bond is still intact, making this the first identification of direct addition to a 5-6 ring fusion in a fullerene, and the first example of an adduct to a 5-6 ring fusion where the ring fusion bond remains intact. The fourth isomer (1d) displayed spectral data consistent with a compound with C1 symmetry and is assigned as an adduct to the C7-C21 bond.

Original languageEnglish
Pages (from-to)2337-2342
Number of pages6
JournalJournal of the American Chemical Society
Volume120
Issue number10
DOIs
StatePublished - Mar 18 1998

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Biochemistry
  • Colloid and Surface Chemistry

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