title: E/Z oxime isomerism in PhC(NOH)CN.
abstract: The reaction of nitric oxide with benzyl cyanide in the presence of potassium methoxide at low temperature gave the dipotassium salt of a bis-diazeniumdiolate 2 in excellent yield. Two new stereospecific syntheses of E or Z 2-(hydroxyimino)-2-phenylacetonitrile from 2 have been found. The thermodynamics of the E/Z isomerization has been investigated spectroscopically in solution, in the solid state by differential scanning calorimetry (DSC), and theoretically in the gas phase. Evidence of catalysis by NO of E/Z oxime isomerization has been observed.
authors: Department of Chemistry, McGill University, 801 Sherbrooke St. W. Montreal, H3A 2K6, Quebec, Canada. scott.bohle@mcgill.ca
authors: D Scott
authors: DS
authors: Bohle
authors: Zhijie
authors: Z
authors: Chua
authors: Inna
authors: I
authors: Perepichka
authors: Kristopher
authors: K
authors: Rosadiuk