Journal of Fluorine Chemistry, volume 59, issue 1, pages 15-31
Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid
1
ICI Chemicals & Polymers Limited, PO Box 8, The Heath, Runcorn, Cheshire, WA7 4QD UK
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Publication type: Journal Article
Publication date: 1992-10-01
Journal:
Journal of Fluorine Chemistry
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.9
ISSN: 00221139
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Abstract
4-Sulpho-2,3,5,6-tetrafluorobenzoic acid ( I ) has been synthesised from pentafluorobenzoic acid via the oxidation of 4-mercapto-tetrafluorobenzoic acid. Reaction of I with DMF/ SOCl 2 gave 1,4-ClC 6 F 4 COCl ( IIA ) which was converted to 1,4-ClC 6 F 4 COF ( IIB ) by fluoride exchange. Reaction with methanol or aniline gave respectively the methyl ester 1,4- ClC 6 F 4 CO 2 Me ( IIIA ) and anilide 1,4-ClC 6 F 4 CONHPh ( IIIB ). Treatment of I with PCl 5 gave the diacid chloride 1,4-ClOCC 6 F 4 SO 2 Cl ( IVA ) which was converted to IIB by the action of KF in tetraglyme. Stoichiometric reaction of I with SF 4 gave 1,4-FOCC 6 F 4 SO 2 F ( IVB ) while the use of excess reagent produced 1,4-F 3 CC 6 F 4 SO 2 F ( V ). Partial hydrolysis of IVB gave 1,4-HO 2 CC 6 F 4 SO 2 F ( VIA ) which was decarboxylated in DMSO to give 1,4- HC 6 F 4 SO 2 F ( VII ). The diacid halides IVA and IVB were readily derivatised with methanol or aniline to give respectively 1,4-MeO 2 CC 6 F 4 SO 2 Cl ( VIIIA ), 1,4-MeO 2 CC 6 F 4 SO 2 F ( VIB ), 1,4-PhNHOCC 6 F 4 SO 2 Cl ( VIIIB ) and 1,4-PhNHOCC 6 F 4 SO 2 F ( VIC ). Treatment of IVB with ethylene glycol gave 1,4-[CH 2 O 2 CC 6 F 4 SO 2 F] 2 ( IX ). Reaction of the methyl esters VIB and VIIIA with equimolar amounts of aniline afforded respectively (3-PhNH)-1,4- MeO 2 CC 6 F 3 SO 2 F ( X ) and 1,4-MeO 2 CC 6 F 3 SO 2 NHPh ( XI ). Analogous reaction of aniline with C 6 F 5 SO 2 F gave 1,4-PhHNC 6 F 4 SO 2 F.
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Citations by publishers
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1 publication, 6.67%
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Walter de Gruyter
1 publication, 6.67%
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1 publication, 6.67%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Fielding H. C., SHIRLEY I. M. Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid // Journal of Fluorine Chemistry. 1992. Vol. 59. No. 1. pp. 15-31.
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Fielding H. C., SHIRLEY I. M. Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid // Journal of Fluorine Chemistry. 1992. Vol. 59. No. 1. pp. 15-31.
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TY - JOUR
DO - 10.1016/s0022-1139(00)80200-6
UR - https://doi.org/10.1016/s0022-1139(00)80200-6
TI - Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid
T2 - Journal of Fluorine Chemistry
AU - Fielding, H C
AU - SHIRLEY, I. M.
PY - 1992
DA - 1992/10/01 00:00:00
PB - Elsevier
SP - 15-31
IS - 1
VL - 59
SN - 0022-1139
ER -
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@article{1992_Fielding,
author = {H C Fielding and I. M. SHIRLEY},
title = {Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid},
journal = {Journal of Fluorine Chemistry},
year = {1992},
volume = {59},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/s0022-1139(00)80200-6},
number = {1},
pages = {15--31},
doi = {10.1016/s0022-1139(00)80200-6}
}
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MLA
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Fielding, H. C., and I. M. SHIRLEY. “Synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid.” Journal of Fluorine Chemistry, vol. 59, no. 1, Oct. 1992, pp. 15-31. https://doi.org/10.1016/s0022-1139(00)80200-6.