A. Zaitsev, R. Méallet-Renault, E. Schmidt
Mar 7, 2005
Citations
0
Influential Citations
27
Citations
Journal
Tetrahedron
Abstract
Abstract 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.