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[60]Fullerene adducts with 9-substituted anthracenes: mechanochemical preparation and retro Diels-Alder reaction |
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| Authors: | Guan-Wu Wang Zhong-Xiu Chen Koichi Komatsu |
| Institution: | a Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China c Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan |
| Abstract: | Three 9-substituted anthracene derivatives, that is, 9-hydroxymethylanthracene (2), 9-methoxymethylanthracene (3) and bis(9-anthrylmethyl) adipate (6), were chosen as the model compounds to evaluate the reactivity in their Diels-Alder reactions with 60]fullerene and in retro Diels-Alder reactions of the formed cycloadducts. Corresponding adducts 4, 5 and 7 were prepared in high yields under solvent-free conditions using high-speed vibration milling technique. In order to determine thermal stabilities of adducts 4, 5 and 7, their dissociations in the temperature range of 40-65 °C were investigated. Fitting the dissociation rates and temperatures to the Arrhenius equation gives the activation energies of 25.8, 21.8 and 24.9 kcal/mol for compounds 4, 5 and 7, respectively. |
| Keywords: | [60]Fullerene anthracene derivatives Diels-Alder reaction Solvent-free Mechanochemical reaction |
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