[2 + 2] photocycloaddition of cyclic enones to C{sub 60}
- New York Univ., New York, NY (United States)
The photocycloaddition cyclic enones to C{sub 60} is a general reaction. The addition was initially explored using a crown ether-tagged C{sub 60} molecule which allows convenient monitoring of the reaction course by electrospray ionization mass spectroscopy (ESI-MS) after complexation with metal ions, usually K{sup +}. A series of experiments in which the concentration of reagents and reaction time were systematically varied established that adduct formation occurs only upon light absorption by the enones. Thus, excitation at 532 nm or in the UV range using low enone: C{sub 60} ratios did not lead to adduct formation. ESI-MS analysis showed that monoaddition was favored at short irradiation times, and that up to seven enone units could be added to a single fullerene molecule upon longer exposure to light. Competitive experiments using 12 different enones indicated that the best product yields were obtained, in decreasing order, with 3-methyl-2-cyclohexen-1-one, isophorone, 2-cyclohepten-1-one, and 2-cyclohexen-1-one. Products isolated from reactions carried out on a larger scale were subjected to spectroscopic analysis ({sup 1}H NMR, {sup 13}C NMR, IR, UV). 34 refs., 7 figs., 2 tabs.
- OSTI ID:
- 282951
- Journal Information:
- Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 24 Vol. 118; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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