One-step Synthesis of Fullerene Hydride C₆₀H₂ via Hydrolysis of Acylated Fullerenes

Abstract

The hitherto unexplored class of acylated fullerene compounds has been shown to be excellent C(60)H2 precursors. Upon a simple treatment with basic Al2O3, they are hydrolyzed quantitatively into C(60)H2. This key feature led to the development of a new, straightforward protocol for the selective synthesis of the simplest [60]fullerene hydride, C(60)H2. This protocol may offer an advantageous alternative to previously known methods for the synthesis of C(60)H2 allowing for a rapid access to C(60)H2 in good yield and high purity without tedious separating processes.

Fullerenes

“…The selective synthesis of 1,2-C 60 H 2 in quantitative yield and high purity has been achieved through hydrolysis of acylated C 60 fullerene in the presence of basic Al 2 O 3 . 47 Products of thermal dehydrogenation of C 60 H 18 at 450-600 1C were studied by spectroscopic techniques. It was found that the complete dehydrogenation of the sample was not achieved, since peaks due to C-H vibrations were still observed even in samples heated at the highest temperatures.…”

Co(I)-Mediated Removal of Addends on the C60 Cage and Formation of the Monovalent Cobalt Complex CpCo(CO)(η2-C60)

“…The retro-Bingel and retro-Diels–Alder (retro-DA) reactions are known as conventional methods for removal of addends on the fullerene cage (Figure a,b). Some reports have appeared on metal-catalyzed, base-assisted, and acid-promoted retro-reactions (Figure c). Our research group has been developing retro-reactions for synthesizing endohedral (hetero)­fullerenes, such as photochemical elimination of an SO unit, carbonyl coupling (using TiCl 4 /Zn, phosphite, or phosphine), and retro-DA reactions.…”

Hydroxyalkylation of [60]fullerene: free radical addition of alcohols to C60

“…20% yield). 8 The formation of this side-product (C 60 H 2 ) may be rationalized by the in situ conversion of 6a to C 60 H 2 , via a base catalyzed elimination of benzaldehyde from 6a. 9,10 In this case, C 60 À anion acts as a good leaving group by virtue of its increased electrophilicity.…”