Organic Magnetic Resonance p. 455 - 459 (1980)
Update date:2022-07-30
Topics:
Crampton, Michael R.
Gibson, Brenda
Metthews, Raymond S.
1H NMR measurements of N-substituted picramides in dimethyl sulphoxide-methanol containing sodium methoxide show that the two major modes of 1:1 interaction involve transfer of an amino proton to give the conjugate base or methoxide attack at the 3-position to give a ?-adduct.The proportion of parent reacting by the latter pathway increases as the proportion of methanol in the solvent increases.Some comparative measurements in isopropanol-dimethyl sulphoxide show that relative to methoxide the isopropoxide ion has a greater propensity abstraction than for base addition.Reaction of the substrates with amide ions derived from piperidine or from benzylamine gives ?-complexes by attack at unsubstituted ring positions.In the benzylamide adducts spin coupling is observed between the amino proton and the adjacent ring and methylene protons.
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