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Issue 20, 2014
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Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

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Abstract

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

Graphical abstract: Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

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Publication details

The article was received on 05 Mar 2014, accepted on 07 Apr 2014 and first published on 07 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00496E
Citation: Org. Biomol. Chem., 2014,12, 3201-3210
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    Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

    S. J. Edeson, J. Jiang, S. Swanson, P. A. Procopiou, H. Adams, A. J. H. M. Meijer and J. P. A. Harrity, Org. Biomol. Chem., 2014, 12, 3201
    DOI: 10.1039/C4OB00496E

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