Abstract
C,N-Diaryl nitrones react rapidly with N-bromosuccinimide in an aprotic solvent to yield among other products, the E and Z isomers of the C-succinimidyl substituted nitrones and a small amount of the corresponding hydroxamic acid. The stereochemistry of the C-succinimidyl nitrones was confirmed by an X-ray structure determination of the C,N-(dimethoxyphenyl) derivative 8e. In the presence of the base DABCO the formation of hydroxamic acids is suppressed and the Z C-succinimidyl nitrone forms more rapidly than the more stable E isomer. Several mechanistic rationalisations of this observed stereochemistry are discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 3833-3841 |
| Number of pages | 9 |
| Journal | Tetrahedron |
| Volume | 39 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 1 Jan 1983 |
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Lobo, A. M., Prabhakar, S., Rzepa, H. S., Skapski, A. C., Tavers, M. R., & Widdowson, D. A. (1983). C-substitution reactions of c,n-diaryl nitrones. Tetrahedron, 39(22), 3833-3841. https://doi.org/10.1016/S0040-4020(01)88625-7