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Dimethyl(2-oxo-2-ferrocenylethyl)sulfonium iodide—a useful synthetic equivalent of ferrocenoylcarbene in the synthesis of ferrocene-containing cyclopropanes |
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| Authors: | Danijela Ili?Ivan Damljanovi? Mirjana Vuki?evi?Volker Kahlenberg Gerhard LausNiko S. Radulovi? Rastko D. Vuki?evi? |
| Affiliation: | a Technical Faculty Kosovska Mitrovica, University of Priština, Kneza Miloša 7, 38220 Kosovska Mitrovica, Serbia b Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovi?a 12, 34000 Kragujevac, Serbia c Department of Pharmacy, Faculty of Medical Sciences, University of Kragujevac, S. Markovi?a 69, 34000 Kragujevac, Serbia d Institute of Mineralogy and Petrography, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria e Institute of Inorganic Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria f Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia |
| Abstract: | The reaction of 1-ferrocenyl-3-thiabutan-1-one with methyl iodide in acetonitrile at room temperature gave dimethyl(2-oxo-2-ferrocenylethyl)sulfonium iodide, which was characterized by spectral data (1H NMR, 13C NMR, IR) and X-ray crystallographic analysis. This salt reacted with a base (sodium hydride) in acetonitrile yielding a stabilized ylide—dimethylsulfonium ferrocenoylmethylide, which was in turn, submitted to reactions with seven conjugated enones. The obtained results showed that this methodology is potentially a new and useful approach to ferrocene-containing cyclopropanes. |
| Keywords: | Ferrocene Sulfonium salt Stabilized sulfur ylide X-ray analysis Conjugated carbonyls Cyclopropanes |
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