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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

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


Authors

David R. Chisholm

Roy Valentine



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 Mar 29, 2024
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

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Accepted Journal Article (1.6 Mb)
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.6b01110.





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