Overall Score3.5
- Understanding Property and Mechanism
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General Characteristics
Oxazole compounds containing a carbonyl group at 4-position are known to undergo thermally driven rearrangement. Thiazoles have the similar property as well.
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General References
- Dewar, M. J. S. J. Am. Chem. Soc. 1974, 96, 6148. DOI: 10.1021/ja00826a030
- Dewar, M.J. S.; Turchi, I. J. J. Org. Chem. 1975, 40, 1521. DOI: 10.1021/jo00898a040
- Corrao, S. L.; Macielag, M. J.; Turchi, I. J. J. Org. Chem. 1990, 55, 4484. DOI: 10.1021/jo00301a056
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Reaction Mechanism
As shown in the above scheme, the formation of ylide intermediate by electrocyclic ring opening has been suggested. (Ref: J. Am. Chem. Soc. 1974, 96, 6148. Chem. Ber. 1971, 104, 1408.)
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Examples
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Experimental Procedure
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Experimental Tips
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References
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Related Reactions
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Related Books
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External Links