7541-02-8Relevant articles and documents
Stereoselective Synthesis of (E)-2-Hydroxyimino-2-phenylacetonitrile by Photolysis of 4-Azido-3-phenylfurazan 2-Oxide
Kunai, Atsutaka,Doi, Takanori,Nagaoka, Takashi,Yagi, Hirofumi,Sasaki, Kazuo
, p. 1843 - 1844 (1990)
Synthesis of (E)-2-hydroxyimino-2-phenylacetonitrile from styrene was examined.This compound was obtained selectively by the photolysis of 4-azido-3-phenylfurazan 2-oxide.
Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones
Mo, Xue-Ling,Chen, Chun-Hua,Liang, Cui,Mo, Dong-Liang
, p. 150 - 159 (2017/11/28)
A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.
E/Z oxime isomerism in PhC(NOH)CN
Bohle, D. Scott,Chua, Zhijie,Perepichka, Inna,Rosadiuk, Kristopher
, p. 4223 - 4229 (2013/05/09)
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. Copyright
