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

Darwish, Adam D, Abdul-Sada, Ala'a K, Avent, Anthony G, Street, Joan M and Taylor, Roger (2003) Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH. Journal of Fluorine Chemistry, 121 (2). pp. 185-192. ISSN 0022-1139

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Abstract

The first fluoroxyfluorofullerene C60F17OF (A) has been isolated from the fluorination of [60]fullerene with a mixture of MnF3 and K2NiF6 at 480degreesC. 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 F-19 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(N)2' substitution of F by OH, followed by oxygen insertion into a 6:5-bond (alphabeta to the OH group) giving a motif not seen previously in fluorofullerenes.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Adam Darwish
Date Deposited: 06 Feb 2012 21:07
Last Modified: 01 May 2012 14:58
URI: http://sro.sussex.ac.uk/id/eprint/29674
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