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 |
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Pages (from-to) | 3833-3841 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 39 |
Issue number | 22 |
DOIs | |
Publication status | Published - 1 Jan 1983 |