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

Chisholm, David R.; Valentine, Roy; Pohl, Ehmke; Whiting, Andrew

Abstract

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.

Citation

Chisholm, D. R., Valentine, R., Pohl, E., & Whiting, A. (2016). Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring. Journal of Organic Chemistry, 81(17), 7557-7565. https://doi.org/10.1021/acs.joc.6b01110

• Journal Article Type: Article
• Acceptance Date: Aug 10, 2016
• Online Publication Date: Jul 28, 2016
• Publication Date: Sep 2, 2016
• Deposit Date: Aug 12, 2016
• Publicly Available Date: Jul 28, 2017
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 81
• Issue: 17
• Pages: 7557-7565
• DOI: https://doi.org/10.1021/acs.joc.6b01110
• Public URL: https://durham-repository.worktribe.com/output/1376569