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Synthesis, structures and some chemical and electrochemical properties of E-1,2-diferrocenyl-3-methylthioprop-2-enone and its ketals
Authors:Tatiana Klimova Berestneva  Marcos Martínez García  Simon Hernández Ortega  Elena Klimova
Institution:a Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P. 04510, México D.F., Mexico
b Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P. 04510, México D.F., Mexico
Abstract:2,3-Diferrocenyl-1-methylthiocyclopropenylium iodide reacts with water, metal alkoxides, phenolates and with alcohols in the presence of Et3N to give E-1,2-diferrocenyl-3-methylthioprop-2-enone or its ketals. Their structures were established based on data from 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The mechanistic aspects of these reactions are discussed. Electrochemical properties of 8 and 13b have been studied. The compounds present two oxidation processes (I-II), attributed to the oxidations of the ferrocenes groups, E0′(I), E0′(II), ΔE0′(II-I) and comproportionation constant Kcom are reported.
Keywords:Ferrocene  Diferrocenyl(methylthio)cyclopropenilium  3  3-Dimethylthio-cyclopropene  1  2-Diferrocenyl-3-methylthioprop-2-enone  Three-membered ring opening
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