Tetrahedron p. 2255 - 2260 (1987)
Update date:2022-09-26
Topics:
Moehrle, H.
Wehefritz, B.
Steigel, A.
The aminolysis of Z-α-halogenoacetophenone oximes results in different mixtures of E- and Z-α-aminoacetophenone oximes depending on the solvent used.Assignment of configuration can be achieved by 13C NMR spectroscopy even if only one isomer is available using a strong solvent dependence of the methylene chemical shift in the case of the Z-isomers.This effect is due to the presence of different conformations in the solvents chloroform and dimethyl sulfoxide.Together with a study by vapor pressure osmometry the results provide an unambiguous proof of intramolecular hydrogen bonding of Z-α-aminoacetophenone oximes in chloroform.
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