Chisholm, David R. and Valentine, Roy and Pohl, Ehmke and Whiting, Andrew (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). pp. 7557-7565.
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.
| Item Type: | Article |
|---|---|
| Full text: | (AM) Accepted Manuscript Download PDF (1588Kb) |
| Status: | Peer-reviewed |
| Publisher Web site: | http://dx.doi.org/10.1021/acs.joc.6b01110 |
| Publisher 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. |
| Date accepted: | 10 August 2016 |
| Date deposited: | 12 August 2016 |
| Date of first online publication: | 28 July 2016 |
| Date first made open access: | 28 July 2017 |
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