Synthesis of prototypical fullerene cyclopropanes and annulenes. Isomer differentiation via NMR and UV spectroscopy

Journal Article · Wed May 24 04:00:00 EDT 1995 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja00125a009· OSTI ID:62308

Smith, III, A B; Strongin, R M; Brard, L; Furst, G T; Romanow, W J ^[1]; Owens, K G; Goldschmidt, R J; King, R C ^[2]

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1. Univ. of Pennsylvania, Philadelphia, PA (United States)
2. Drexel Univ., Philadelphia, PA (United States)

Parent cyclopropanes, annulenes, and related derivatives of C{sub 60} and C{sub 70} have been prepared and subjected to extensive spectroscopic scrutiny. Photolysis of the diazomethane adduct of C{sub 60} afforded the C{sub 61}H{sub 2} cyclopropane 2, accompanied by the isomeric annulene 4. Reaction of dimethyldiazomethane with C{sub 60} led to C{sub 63}H{sub 6} annulene 11, which upon heating was smoothly converted to the cyclopropane isomer 10 with an activation energy of 25 {+-} 1 kcal-mol{sup -1}. Addition of diazomethane to a toluene solution of C{sub 70} generated a 12:1:2 mixture of pyrazolines. Photolysis of the mixture gave the C{sub 11}H{sub 2} cyclopropanes 6 and 7, whereas thermolysis furnished the isomeric annulenes 8 and 9. Criteria have been developed for distinguishing fullerene cyclopropane derivatives from the corresponding annulenes via NMR and UV spectroscopy. 57 refs., 12 figs., 1 tab.

• Sponsoring Organization: USDOE
• OSTI ID: 62308
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 20 Vol. 117; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
66 PHYSICS
CARBON
FULLERENES
ISOMERS
LASERS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
SYNTHESIS
TIME-OF-FLIGHT MASS SPECTROMETERS
ULTRAVIOLET SPECTRA