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The stable diene adduct 1 can be prepared in good yield when C60 is treated with o-quinodimethane in toluene. o-Quinodimethane is generated in situ from 1,2-bis(bromomethyl)benzene and KI in the presence of [18]crown-6 as phase-transfer catalyst. Adduct 1 was isolated after gel-permeation chromatography, and characterized by mass spectrometry and NMR spectroscopy; the sketch shows its geometry-optimized structure.
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Belik et al. (1993) studied this question.
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