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1H NMR utilization of through-space effects: III—configuration of oximes and analogous compounds

✍ Scribed by M. Rouillard; Y. Girault; M. Decouzon; M. Azzaro

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
353 KB
Volume
21
Category
Article
ISSN
0749-1581

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✦ Synopsis

The configurational assignment of 2 and E nitrogen derivatives (>C=N--Y) of 3,5,5-trimethyl-2cyclohexen-1-one was made taking into consideration the through-space effects on oxime, 0-methyloxime, dimethylhydrazone, tert-butylimine, N,N,N-trimethylhydrazonium iodide and oxime hydrochloride derivatives. The relationship between the magnitude of the chemical shifts of the a-protons and the dihedral angle formed by the or-C-H bond and the C=N-OH plane was interpreted in terms of the geometrical dependence of the electric field effect. For the different Y substituents, the change in chemical shift between the Z and the E configuration of the proton near the functional group was mainly dependent on the electric field effect.

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