C-substitution reactions of c,n-diaryl nitrones

Ana M. Lobo, Sundaresan Prabhakar, Henry S. Rzepa, Andrej C. Skapski, M. Regina Tavers, David A. Widdowson

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12 Citations (Scopus)

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 languageEnglish
Pages (from-to)3833-3841
Number of pages9
JournalTetrahedron
Volume39
Issue number22
DOIs
Publication statusPublished - 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