Editing Buckminsterfullerene (section)

=== Hydrogenation ===
C<sub>60</sub> exhibits a small degree of aromatic character, but it still reflects localized double and single C–C bond characters. Therefore, C<sub>60</sub> can undergo addition with hydrogen to give polyhydrofullerenes. C<sub>60</sub> also undergoes [[Birch reduction]]. For example, C<sub>60</sub> reacts with lithium in liquid ammonia, followed by ''tert''-butanol to give a mixture of polyhydrofullerenes such as C<sub>60</sub>H<sub>18</sub>, C<sub>60</sub>H<sub>32</sub>, C<sub>60</sub>H<sub>36</sub>, with C<sub>60</sub>H<sub>32</sub> being the dominating product. This mixture of polyhydrofullerenes can be re-oxidized by [[2,3-Dichloro-5,6-dicyano-1,4-benzoquinone|2,3-dichloro-5,6-dicyano-1,4-benzoquinone]] to give C<sub>60</sub> again.

A selective hydrogenation method exists. Reaction of C<sub>60</sub> with 9,9′,10,10′-dihydroanthracene under the same conditions, depending on the time of reaction, gives C<sub>60</sub>H<sub>32</sub> and C<sub>60</sub>H<sub>18</sub> respectively and selectively.<ref name="InorgChem">{{cite book| title = Inorganic Chemistry| edition = 3rd| chapter = Chapter 14: The group 14 elements| author1 = Catherine E. Housecroft| author2 = Alan G. Sharpe| publisher = Pearson| year = 2008| isbn = 978-0-13-175553-6}}</ref>