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Synthesis of new perchlorates from 4- nitropyridine 1-oxide by acylation and decarboxylation
Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
2011 (English)Independent thesis Advanced level (degree of Master (One Year)), 20 credits / 30 HE creditsStudent thesis
Abstract [en]

4-Nitropyridine 1-oxide was reacted with bis(trichloromethyl) carbonate, carbonyl fluoride, methyland ethyl chloroformate. Of particular interest was to examine if denitrohalogenation occurs when 4-nitropyridine 1-oxide is treated with carbonyl fluoride which happens when 4-nitropyridine 1-oxidereacts with bis(trichloromethyl) carbonate. A reaction took place but what was formed is still amatter of question.

Two new compounds, 1-(methyloxycarbonyloxy)- and 1-(ethyloxycarbonyloxy)-4-nitropyridiniumperchlorate were obtained when 4-nitropyridine 1-oxide and sodium perchlorate in acetonitrile werereacted with methyl and ethyl chloroformate, respectively.

1-Ethyloxy-4-nitropyridinium perchlorate were formed when heating 1-(ethyloxy-carbonyloxy)-4-nitropyridinium perchlorate. The evolution of carbon dioxide ceased at 90 OC. The structuredetermination of the product was made by IR and1H-NMR spectroscopy. The methyl analogue onthe other hand was completely decarboxylated at 145 OC according to an IR spectrum. The finalstructure determination of the latter compound remains to be done. Both compounds are new.

Experiments were also done in order to work out a simple method for synthesizing carbonyl fluoridefrom bis(trichloromethyl) carbonate and potassium fluoride using 18-crown-6 or tetrabutylammoniumbromide as phase transfer catalysts in several solvents, e.g. acetonitrile, nitromethane, propylenecarbonate. Carbonyl fluoride was formed but its purity remains to be settled.

Place, publisher, year, edition, pages
2011. , p. 25
National Category
Other Basic Medicine
Identifiers
URN: urn:nbn:se:lnu:diva-12498OAI: oai:DiVA.org:lnu-12498DiVA, id: diva2:422901
Subject / course
Chemistry
Uppsok
Physics, Chemistry, Mathematics
Supervisors
Examiners
Available from: 2011-06-21 Created: 2011-06-14 Last updated: 2018-01-12Bibliographically approved

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