Journal of the Chemical Society. Chemical communications p. 2325 - 2326 (1995)
Update date:2022-08-03
Topics:
Evans
Holmes
Collins
Raithby
Russell
The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative as well as two unexpected products; the major product (resulting from a selenium re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide) with the largest p-orbital distortion (τ = 50.6°) recorded for a cyclic amide.
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