Publication details for Prof. Ehmke PohlChisholm, 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.
- Publication type: Journal Article
- ISSN/ISBN: 0022-3263 (print), 1520-6904 (electronic)
- DOI: 10.1021/acs.joc.6b01110
- Further publication details on publisher web site
- Durham Research Online (DRO) - may include full text
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.