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15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers

✍ Scribed by Xiaohong Liu; Xiaohua Stella Huang; Ny Sin; Brian L. Venables; Vikram Roongta

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
100 KB
Volume
48
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

In this article, we describe the characteristic ^15^N chemical shifts of isatin oxime ethers and their isomer nitrone. These oxime ethers and nitrones are the alkylation reaction products of isatin oximes. In our study, the ^15^N chemical shifts observed in these oxime ethers were in the 402–408 (or 22–28) ppm range, although those for their corresponding nitrone series were in the 280–320 (or −100 to −60) ppm range. This remarkable difference in ^15^N NMR chemical shift values could potentially be used to determine the O‐ versus N‐alkylation of oximes, even when only one isomer is available. In this paper, the differences in ^15^N NMR chemical shifts serve as the basis for a discussion about how to distinguish both regioisomers derived from the oximes alkylation. Copyright © 2010 John Wiley & Sons, Ltd.

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