Polyhalogenated heterocyclic compounds Part 52. Macrocycles from 3,5-dichloro-2,4,6-trifluoropyridine

Model studies show that displacement of fluorine, rather than chlorine, occurs upon reaction of 3,5-dichloro-2,4,6-trifluoropyridine with sodium methoxide and phenoxide. Subsequent hydro-dechlorination can be achieved by reaction with lithium aluminium hydride whereas reaction of sodium in iso-propa...

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Bibliographic Details
Published inJournal of fluorine chemistry Vol. 126; no. 7; pp. 1002 - 1008
Main Authors Chambers, RD, Khalil, A, Murray, CB, Sandford, G, Batsanov, AS, Howard, JAK
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier 01.07.2005
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
pyridine
macrocycle
nucleophilic aromatic substitution
heterocycle
perfluoroheterocycle
X-ray structure
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Summary:Model studies show that displacement of fluorine, rather than chlorine, occurs upon reaction of 3,5-dichloro-2,4,6-trifluoropyridine with sodium methoxide and phenoxide. Subsequent hydro-dechlorination can be achieved by reaction with lithium aluminium hydride whereas reaction of sodium in iso-propanol leads to formation of the tri-iso-propoxy pyridine derivative, via nucleophilic substitution of the methoxy group, rather than the dechlorinated products. Macrocycles can be synthesised by reactions of appropriate difunctional oxygen nucleophiles with 3,5-dichloro-2,4,6-trifluoropyridine, one of which was characterised by X-ray crystallography. (c) 2005 Elsevier B.V. All rights reserved.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2005.01.018