Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring

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• 作者：David R. Chisholm ; Roy Valentine ; Ehmke Pohl ; Andrew Whiting
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：81
• 期：17
• 页码：7557-7565
• 全文大小：419K
• 年卷期：0
• ISSN：1520-6904

文摘

A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant aniline-derived enaminones was explored through NMR, FTIR and X-ray crystallography. A straightforward purification protocol that employs direct Kugelrohr distillation was identified, and the method was further extended to other amines and ynones, allowing rapid access to these interesting compounds.