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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. 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
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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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