Journal of Organic Chemistry p. 764 - 767 (1989)
Update date:2022-09-26
Topics:
Perrin, Charles L.
Thoburn, John D.
Kinetics of E/Z stereoisomerization of N-arylformimidate anions, HC(O-)=NAr, in N-methylpropionamide solvent were determined by an NMR saturation-transfer method.A Hammett plot of the rate constans gives a slope ρ of +2.3 +/- 0.2 or +2.1 +/- 0.3.This value is very close to the ρ of 2.2 observed in similar imine stereoisomerizations know to proceed by nitrogen inversion.It is inconsistent with the ρ of 3.8 expected for stereoisomerization by C-N rotation.It is therefore concluded that E/Z stereoisomerization of imidate anions proceeds by nitrogen inversion, despite a high-level MO calculation that favored C-N rotation.
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