Tetrahedron p. 3833 - 3842 (1983)
Update date:2022-08-05
Topics:
Lobo, Ana M.
Prabhakar, Sundaresan
Rzepa, Henry S.
Skapski, Andrzej C.
Tavares, M. Regina
Widdowson, David A.
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 sterochemistry of the C-succinimidyl niyrones 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.
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