Journal of Organic Chemistry p. 3618 - 3620 (1980)
Update date:2022-08-05
Topics:
Jones, Paul R.
Weisman, Gary R.
Baillargeon, Maurice J.
Gosink, Thomas A.
A series of o-arylacetyl-N,N-dimethylbenzamides, 1-7, being studied as models for chain tautomers, differed markedly in their 1H NMR spectral properties, as a function of the substituents R1-R4.In the two cases where substituents were placed ortho to the amide group, the benzylic protons were anisochronous at ambient temperatures.Reported dynamic 1H NMR results are consistent with concomitant C-N and aryl-CO torsional processes.The 13C carbonyl shifts are compared with those of model compounds.
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