Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH

Darwish, A.D., Abdul-Sada, A.K., Avent, A.G., Street, J.M. and Taylor, R. (2003) Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH. Journal of Fluorine Chemistry, 121 (2), 185-192. (doi:10.1016/S0022-1139(03)00014-9).

Abstract

The first fluoroxyfluorofullerene C₆₀F₁₇OF (A) has been isolated from the fluorination of [60]fullerene with a mixture of MnF₃ and K₂NiF₆ at 480ºC. This compound has a shorter HPLC retention time than the isomeric fluorofullerene ethers (oxahomofullerenes) and is less stable towards El mass spectrometry. It fragments by losing OF as a single entity and shows no formation of C₆₀O as a fragment ion. By contrast, the ethers fragment by first losing a number of F atoms and then CO, and ultimately show also the presence of C₆₀O, whilst epoxides lose CO as a main fragmentation step and do not give C₆₀O. The first oxahomofluorofullerenol C₆₀F₁₇O.OH (B) has been isolated from the UV-irradiation of a toluene solution of C₆₀F₁₈ in air during 65 It and readily eliminates HF due to adjacent F and OH groups during El mass spectrometry. The structures of both the compounds have been deduced from I D and 2D ¹⁹F NMR spectroscopy. Just as oxygen inserts into FC-CF bonds of C₆₀F₁₈ to give ethers, so insertion into a C-F bond gives A. The oxahomofluorofullerenol B is produced by S_N2' substitution of F by OH, followed by oxygen insertion into a 6:5-bond (αβ to the OH group) giving a motif not seen previously in fluorofullerenes.

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