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C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of 'missing' fluorine through restricted rotation of a phenyl group

C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of 'missing' fluorine through restricted rotation of a phenyl group
C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of 'missing' fluorine through restricted rotation of a phenyl group
From the reaction of C60F18 with benzene in the presence of SbCl5 we have isolated a compound of 1252 amu indicated to be C60F14OFPh3, a fluoroxyfullerene. Temperature-variable H-1 NMR shows that one phenyl group suffers restricted rotation on cooling to 218 K, attributed to the presence of the OF group which, as in the case of the recently characterised C60F17OF, fails to give a signal for this group in the F-19 NMR. We have isolated also, C60F14O2FPh3 (1268 amu) a mixture of oxahomo derivatives Of C60F14OFPh3 arising from oxygen insertion into FC-CF bonds. Theoretical calculations for C60F14OFPh3 indicate that the phenyl group nearest to the OF group is twisted out of the plane containing the other two.
fullerenes, arylfullerenes, fluoroxyfluorofullerenes, fluorine nmr, ethersspectroscopic characterization, 1st, epoxides, isomers
0022-1139
1131-1136
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Darwish, Adam D., Avent, Anthony G., Gol'dt, Ilya V., Street, Joan M. and Taylor, Roger (2004) C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of 'missing' fluorine through restricted rotation of a phenyl group. Journal of Fluorine Chemistry, 125 (7), 1131-1136. (doi:10.1016/j.jfluchem.2004.02.007).

Record type: Article

Abstract

From the reaction of C60F18 with benzene in the presence of SbCl5 we have isolated a compound of 1252 amu indicated to be C60F14OFPh3, a fluoroxyfullerene. Temperature-variable H-1 NMR shows that one phenyl group suffers restricted rotation on cooling to 218 K, attributed to the presence of the OF group which, as in the case of the recently characterised C60F17OF, fails to give a signal for this group in the F-19 NMR. We have isolated also, C60F14O2FPh3 (1268 amu) a mixture of oxahomo derivatives Of C60F14OFPh3 arising from oxygen insertion into FC-CF bonds. Theoretical calculations for C60F14OFPh3 indicate that the phenyl group nearest to the OF group is twisted out of the plane containing the other two.

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More information

Published date: 1 July 2004
Keywords: fullerenes, arylfullerenes, fluoroxyfluorofullerenes, fluorine nmr, ethersspectroscopic characterization, 1st, epoxides, isomers

Identifiers

Local EPrints ID: 20181
URI: http://eprints.soton.ac.uk/id/eprint/20181
ISSN: 0022-1139
PURE UUID: a5388882-5cea-4ab5-9ace-877325ae8374

Catalogue record

Date deposited: 22 Feb 2006
Last modified: 15 Jul 2019 19:25

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