Evidence of Restricted Rotation about the N—C Bond in 2: 6-Disubstituted Acetanilides

Abstract

THE failure1 to effect optical resolution of substituted anilines having two large ortho groups has left unconfirmed the theoretical possibility of restricted rotation about the nitrogen-nuclear single bond in such compounds. That such steric effects are indeed present in suitably constituted molecules is now proved by a method entirely independent of optical activity.

References

  1. 1

    Tuan, Hsü, and Hsü, J. Chinese Chem. Soc., 4, 131 (1936).

  2. 2

    Chaplin and Hunter, J. Chem. Soc., 1114 (1937).

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HUNTER, L., CHAPLIN, H. Evidence of Restricted Rotation about the N—C Bond in 2: 6-Disubstituted Acetanilides. Nature 140, 896 (1937). https://doi.org/10.1038/140896a0

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