575444-53-0Relevant academic research and scientific papers
Transylidation of 3-methyl-phenacylpyridazinium ylides with phenylisocyanate. Influence of triethylamonium cation over prototropic rearrangement
Ivanov, Daniela,Petrovanu, Magda,Constantinescu, Mircea
, p. 261 - 268 (2012/07/03)
Monosubstituted 3-methyl-phenacylpyridazinium ylides when treated in situ with phenylisocyanate in the presence of triethylamine give an intermediate that undergoes a prototropic rearrangement to the final disubstituted ylides. In order to gain further insight into the mechanism corresponding to the influence of triethylamine, three possible pathways were investigated, in the absence of tertiary base, in the presence of triethylamine, and via triethylamonium bromide by-product. It was our hypothesis that the presence of triethylamine in reacting mixture is responsible for reaction to take place. Indeed, theoretical study at B3LYP level of computation indicated triethylamonium catalyst as particular effective in this reaction for prototropy. Theoretical findings are consistent with the experimental study results.
