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Electrophilic substitution of C60F18 into phenols: HF elimination between OH and a 1,3-shifted fluorine giving benzofurano[2',3':10,26]hexadecafluro[60]fullerene and derivatives

Electrophilic substitution of C60F18 into phenols: HF elimination between OH and a 1,3-shifted fluorine giving benzofurano[2',3':10,26]hexadecafluro[60]fullerene and derivatives
Electrophilic substitution of C60F18 into phenols: HF elimination between OH and a 1,3-shifted fluorine giving benzofurano[2',3':10,26]hexadecafluro[60]fullerene and derivatives
The reaction of C60F18 with phenol, 2-naphthol and quinol in the presence of ferric chloride leads to initial electrophilic substitution (aryldefluorination). This occurs at both ortho and para positions for phenol, at the ortho position for quinol, and at the relatively hindered but most reactive 1-position for 2-naphthol. It is followed, where sterically favourable, by HF loss either between the OH group and F (rendered adjacent as a result of a 1,3-shift) or to attack of the OH group at an adjacent double bond with loss of a beta-fluorine, giving benzofurano[2',3':10,26]hexadecafluoro[60]fullerene derivatives. The reaction is accompanied by some complete defluorination leading, in reaction with phenol and with 2-naphthol, to the formation of benzofurano[2',3':1,2][60]fullerene and naphtho[2,1:b]furano[d:1,2][60]-fullerene, respectively. The mechanism of base-catalysed reaction of phenols with C60Cl6 is re-evaluated.
aromatic-substitution, spontaneous oxidation, fullerene, fullerenes, c60cl6, arylation, c-58
1477-0520
1764-1768
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
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
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Darwish, Adam D., Avent, Anthony G., Street, Joan M. and Taylor, Roger (2003) Electrophilic substitution of C60F18 into phenols: HF elimination between OH and a 1,3-shifted fluorine giving benzofurano[2',3':10,26]hexadecafluro[60]fullerene and derivatives. Organic and Biomolecular Chemistry, 1 (10), 1764-1768. (doi:10.1039/b301528a).

Record type: Article

Abstract

The reaction of C60F18 with phenol, 2-naphthol and quinol in the presence of ferric chloride leads to initial electrophilic substitution (aryldefluorination). This occurs at both ortho and para positions for phenol, at the ortho position for quinol, and at the relatively hindered but most reactive 1-position for 2-naphthol. It is followed, where sterically favourable, by HF loss either between the OH group and F (rendered adjacent as a result of a 1,3-shift) or to attack of the OH group at an adjacent double bond with loss of a beta-fluorine, giving benzofurano[2',3':10,26]hexadecafluoro[60]fullerene derivatives. The reaction is accompanied by some complete defluorination leading, in reaction with phenol and with 2-naphthol, to the formation of benzofurano[2',3':1,2][60]fullerene and naphtho[2,1:b]furano[d:1,2][60]-fullerene, respectively. The mechanism of base-catalysed reaction of phenols with C60Cl6 is re-evaluated.

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More information

Published date: 21 May 2003
Keywords: aromatic-substitution, spontaneous oxidation, fullerene, fullerenes, c60cl6, arylation, c-58

Identifiers

Local EPrints ID: 19943
URI: https://eprints.soton.ac.uk/id/eprint/19943
ISSN: 1477-0520
PURE UUID: ece384e7-0eb8-43d0-bf09-16c659a1ad88

Catalogue record

Date deposited: 24 Feb 2006
Last modified: 17 Jul 2017 16:30

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