FORMATION OF METHYLENE DERIVATIVES OF [60]-FULLERENES, [70]-FULLERENES, [78]-FULLERENES AND [84]-FULLERENES BY REACTION OF FULLERENE-CONTAINING SOOT EXTRACT WITH TETRAHYDROFURAN

If a mixture of carbon clusters extracted from soot produced by the ar e-discharge procedure is either heated or sonicated with tetrahydrofur an (THF), a range of methylene derivatives C-m[CH2](n), where m is 60, 70. 78 or 84 and n is variously 1-6 are produced. These results const itute the first formation of [78]fullerene derivatives; [76]fullerene does not appear to react under these conditions. Species with n = 3 ar e dominant, believed to be due to addition of trimethylene chains, thr ough loss of formaldehyde from THF. This conclusion is supported by th e prominence of [CH2](4) adducts in the product if [60]fullerene is he ated under reflux with dihydropyran. Reaction of pure[60]fullerene wit h THF results in the addition of up to 10 methylene groups to the cage .