Journal article
Carboxyketenes from 4-Hydroxy-1,3-oxazin-6-ones and Meldrum's Acid Derivatives
The Journal of Organic Chemistry, Vol.72(4), pp.1399-1404
2007
Abstract
New 4-hydroxy-1,3-oxazin-6-ones 8 and 16 were prepared from chlorocarbonyl(phenyl)ketene and amides. The flash vacuum thermolysis (FVT) reactions of these compounds and the 4-methoxy derivative 17 were investigated by Ar matrix isolation IR spectroscopy and online mass spectrometry including MS/MS analysis. Carboxy(phenyl)ketene 10 is formed as the major product by thermal fragmentation of 4-hydroxy-1,3-oxazin-6-one 8. This takes place via the unstable 6-hydroxy tautomer 9. Another tautomer, the 5H-isomer 12, leads to the formation of benzoyl isocyanate 13 as a minor product together with phenylketene 14. Carboxy(phenyl)ketene 10 remains detectable at high FVT temperatures but undergoes thermal decarboxylation to phenylketene 14. The same carboxy(phenyl)ketene 10 is also produced in significant amounts by FVT of 5-phenyl-Meldrum's acid 18 via the unstable enol tautomer 19. A small amount of the unsubstituted carboxyketene 20 is observable on FVT of Meldrum's acid 1 itself.
Details
- Title
- Carboxyketenes from 4-Hydroxy-1,3-oxazin-6-ones and Meldrum's Acid Derivatives
- Authors/Creators
- L. George (Author/Creator) - University of MonsR.N. Veedu (Author/Creator) - University of MonsH. Sheibani (Author/Creator) - University of MonsA.A. Taherpour (Author/Creator) - University of MonsR. Flammang (Author/Creator) - University of MonsC. Wentrup (Author/Creator) - University of Mons
- Publication Details
- The Journal of Organic Chemistry, Vol.72(4), pp.1399-1404
- Publisher
- ACS Publications
- Identifiers
- 991005541404007891
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
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- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.171 Green Heterocycle Synthesis
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry