Fullerene monoalkylated

There are limited number of reports of the observation and isolation of functionalized fullerene cations. The monoalkylated [RC6o+(73,74), C12CH-C70+ (75), and (EtO)2P+(OH)CH2-C60+ (76)], monoprotonated [HC60+ (7-2,77)], and pentaarylated [Ar5C60+ (75)] fullerene cations have thus far been prepared as stable solutions or isolated as solids (Figure 1). 

Sun et al. further investigated the photoinduced electron transfer reactions of C6o and triethylamine, both in deoxygenated solution and air saturated solution [79], Three types of cycloadducts of fullerenes 33 and 92a-b were obtained, whereas the formation of the monoalkylated l,2-dihydro[60]fullerene 29 as described by Liou et al. [230] in the reaction of trimethylamine and /V,/V-dimcthy-laniline with C6o, was not observed (see Fig. 32). 

Scheme 343 The reaction of alkyl bromides to fullerenes yielding monoalkylated addition products by using catalytic amounts of Co in the presence of Mn.

Similarly, 12a-d and 14 are hydrolyzed cleanly to the corresponding fiillerenols, 2a-d and 8 (Scheme 9.12), when their solutions in CS2 or benzene are passed through a column of silica gel [9, 15]. As previously described, these fiillerenols are excellent precursors for the study of monoalkylated fullerene cations under stable-ion conditions. 

SCHEME 25 Irradiation of ketone 56 and Cg, leading to monoalkyl-1,2-dihydro-[60]fullerene 59. 

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