69688-80-8Relevant academic research and scientific papers
CYCLIZATION OF HYDROXYIMINO-β-DICARBONYL COMPOUNDS WITH KETONES UNDER THE INFLUENCE OF ALKALI-METAL ALKOXIDES
Belyaev, E. Yu.,El'tsov, A. V.,Kochetkov, B. B.,Orlovskaya, N. F.,Tovbis, M. S.
, p. 1299 - 1304 (2007/10/02)
Investigation of the condensation of hydroxyimino-β-dicarbonyl compounds with acetone in the presence of sodium ethoxide by a spectrophotometric methods showed that the accumulation rate of 3,5-dimethyl-2-nitrosophenol in the reaction of hydroxyiminoacetylacetone with acetone increases with increase in the sodium ethoxide concentration.In the transition to arylated hydroxyimino-β-diketones p-nitrosophenols are formed exclusively and the reaction rate decreases, but increase in the electron-withdrawing characteristics of the substituent in the benzene ring of the hydroxyimino-β-dicarbonyl compound leads to an increase in the cyclization rate.For the case of the condensation of hydroxyiminoacetylacetone with acetone and methyl ethyl ketone an increase was found in the ratio of the para and ortho isomers of the nitrosophenols with decrease in the radius of the alkali metal, with substitution of potassium ethoxide by the alkoxides of tertiary alcohols, and with the use of solvents not containing hydroxyl group ( DMSO ).On the basis of the obtained data an improved preparative method was developed for the synthesis of p-nitrosophenols.A series of 2,3,5-trialkylnitrosophenols and previously unobtainable 3,5-di(aryl)heterylnitrosophenols were obtained.
