850130-93-7Relevant academic research and scientific papers
Synthesis of 2-mesityl-3-methylpyrrole via the Trofimov reaction for a new BODIPY with hindered internal rotation
Zaitsev, Alexey B.,Méallet-Renault, Rachel,Schmidt, Elena Yu.,Mikhaleva, Al'bina I.,Badré, Sophie,Dumas, Cécile,Vasil'tsov, Alexander M.,Zorina, Nadezhda V.,Pansu, Robert B.
, p. 2683 - 2688 (2005)
The reaction of E-ethylmesitylketoxime with acetylene in the system KOH/DMSO (the Trofimov reaction) (70-74°C, 3 h, atmosphere pressure) affords 2-mesityl-3-methylpyrrole (23%), 2-mesityl-3-methyl-1-vinylpyrrole (8%), Z- (5%) and E- (2%) isomers of O-vinylethylmesitylketoxime. Initial ethylmesitylketoxime was prepared in two ways: via very slow oximation of ethylmesitylketone in 30% yield after 8 months, and, more efficiently, by oximation of ethylmesitylketimine hydrochloride derived from bromomesitylene in several steps. 2-Mesityl-3-methylpyrrole was used for the synthesis of 4,4-difluoro-2,6-dimethyl-3,5,8-trimesityl-4-bora-3a,4a-diaza-s-indacene with mesityl substituents having hindered internal rotation and preventing π-stacking at high concentrations. The latter factor enables the fluorescence of crystals of the prepared BODIPY, a feature that was not previously documented for such molecules.
