Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 11, Pages 5652-5657Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00594
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Funding
- Kyoto University [24245005, 26105733, 15H02158]
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [15H02158, 26105733] Funding Source: KAKEN
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The Passerini reaction mechanism is revisited using high-level DFT calculations. Contrary to the common belief, the nitrilium intermediate is found to be stable in solution and its formation is rate-determining. The present results point out that this step is catalyzed by a second carboxylic acid molecule, as the subsequent Mumm rearrangement is. The solvent effect on the reaction rate was investigated: In a protic solvent like methanol, hydrogen bonds are responsible of the increasing barrier of the rate-determining step, compared to the commonly used solvent, the dichloromethane.
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