5467-94-7Relevant academic research and scientific papers
Reaction of hydroxyiminoacetophenone with p-toluenesulfonyl chloride and an X-ray diffraction study of the reaction product
Fedorov,Nesterov,Shestopalo
, p. 838 - 840 (1997)
2-Benzoyloxy-2-phenylmalononitrile is formed instead of the expected oxime tosylate in the reaction of hydroxyiminoacetophenone with p-toluenesulfonyl chloride. The structure of the product was confirmed unambiguously by X-ray diffraction analysis.
Ortho Amides, XLVI. - Contributions to the Chemistry of Bis(dialkylamino)malononitriles
Kantlehner, Willi,Greiner, Ulrich
, p. 965 - 973 (2007/10/02)
The reaction of chloroformamidinium chlorides 2 with sodium cyanide in the two-phase system ether/water affords bis(dialkylamino)malononitriles 3 with good yields.From 3a and morpholine or aniline the guanidines 5 and 6 can be obtained, respectively.Alcohol-free sodium ethoxide transforms 3a into the urea acetal 10b, whereas in the reaction of 3a with alkoxides in alcohol ortho carbamic esters 11a, b are produced.The malonic esters and acetoacetic esters 12 react with 3a in the presence of two equivalents of sodium hydride to give the ketene aminals 13.The reactionof 3a with malononitrile furnishes the guanidinium salt 14, which cyclized by hydrogen chloride to the pyridinetricarbonitrile 15.In the presence of sodium hydride, 3a and malononitrile or cyanoacetic esters 17 from the ketene aminal 16 and the 1,2,3-tricyanopropenides 18a-c, respectively.The analogous salts 20 and 21 result from the reaction of 3a with the barbituric acid derivatives 19a, and b, respectively.Hydrogen chloride reacts in ether with 3a to afford the piperazinetetracarbonitrile 22.Reaction of carboxylic acid chlorides yields the cyanoformamidinium salt 28a; byproducts are acyl cyanides 29 and dimeric acyl cyanides 30.Triethyloxonium tetrafluoroborate transforms 3a into the salt 28b.Bromine and iodine react with 3a to produce the salts 28c, d and 28e, f, respectively, depending on the stoichiometric ratios of the starting materials.The thiocyanate 28g is prepared from sulfur and 3a.
Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides
Sukata, Kazuaki
, p. 1085 - 1090 (2007/10/02)
The effects of alkali metal cyanide impregnated on Amberlite XAD resins (KCN/XAD, NaCN/XAD) have been examined using the cyanation of benzoyl chloride.In benzene, benzoyl cyanide was obtained in a very high yield with high selectivity under mild conditions.It is proposed that the reaction occurs on the surface of the resin.On the basis of the result obtained in the absence of any solvent, the reactivity of KCN/XAD toward dimerization of benzoyl cyanide has been found to be much poorer than that of KCN in solution.Although the reaction of acyl chlorides with KCN/XADor NaCN/XAD in benzene gave various acyl cyanides in good to excellent yields, no aliphatic acyl cyanide could be obtained.
CATALYTIC AND STOICHIOMETRIC TRANSFORMATIONS WITH TRIPHENYL(P,P,P-TRIPHENYLPHOSPHINE IMIDATO-N) PHOSPHORUS CYANIDE,
Dillon, Keith B.,Hodgson, Martin,Parker, David
, p. 849 - 854 (2007/10/02)
Reactions involving anhydrous +CN-, 1, are described for a series of nucleophilic displacements.The reagent may be used stoichiometrically with moisture sensitive substrates, and also acts as an efficient phase transfer catalyst.
