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Durham University

Department of Biosciences


Publication details for Prof. Ehmke Pohl

Chisholm, David R., Valentine, Roy, Pohl, Ehmke & Whiting, Andrew (2016). Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring. The Journal of Organic Chemistry 81(17): 7557-7565.

Author(s) from Durham


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.