O. V. Boltalina , T. Drewello, A. Hirsch, T. J. D. Jorgensen, V. Yu. Markov, U. Reuther, R. Taylor
"Fullerenes. Recent advances in the chemistry and physics of fullerenes and related materials", edited by Prashant V. Kamat, Dirk M. Guldi and Karl M.Kadish, published by: the Electrochemical Society, Inc. 10 South Main Street, Pennington, New Jersey, v.7, p. 462-471, (1999).
ABSTRACT. Aza[60]fullerene has been fluorinated with the transition metal fluorides: MnF3 and CeF4, and in each case, the most prominent species in the volatile products is C59NF33, as shown by electron impact mass spectrometry. Thus, wheras fluorination of [60]fullerene with these reagents produced C60F36, fluorination of aza[60]fullerene results in the addition only 33 fluorines. This may be due to replacement of C-F by N (in one of the pentagonal rings in C60F36 that has three attached fluorines) and loss of 2F giving a second double bond, thereby creating an aromatic (6
) structure of high stability. The positive ion laser-desorption ionization mass spectra of the fluorinated products showed the presence of ions due to the aza derivatives of the higher fullerenes, and thus provides the first detection of this species.