Formation of methylene derivatives of [60]-, [70]-, [78]- and [84]-fullerenes by reaction of fullerene-containing soot extract with tetrahydrofuran

Birkett, Paul R., Darwish, Adam D., Kroto, Harold W., Langley, G. John, Taylor, Roger and Walton, David R.M. (1995) Formation of methylene derivatives of [60]-, [70]-, [78]- and [84]-fullerenes by reaction of fullerene-containing soot extract with tetrahydrofuran. Journal of the Chemical Society, Perkin Transactions 2, (3), 511-514. (doi:10.1039/p29950000511).

Abstract

If a mixture of carbon clusters extracted from soot produced by the arc-discharge procedure is either heated or sonicated with tetrahydrofuran (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 constitute the first formation of [78]fullerene derivatives; [76]fullerene does not appear to react under these conditions. Species with n = 3 are dominant, believed to be due to addition of trimethylene chains, through loss of formaldehyde from THF. This conclusion is supported by the prominence of [CH₂]₄ adducts in the product if [60]fullerene is heated under reflux with dihydropyran. Reaction of pure [60]fullerene with THF results in the addition of up to 10 methylene groups to the cage.

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Contributors

Author: G. John Langley

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