Alkylation of ferrocene with tetrachlorocyclopropene in the presence of AlCl3 followed by aqueous workup affords 2,3-diferrocenylcyclopropenone in high yield. We have studied some of this ketone's chemical transformations and electrochemical properties. 2,3-Diferrocenylcyclopropenone withstands thermolysis; it is stable in an acidic medium; the action of tetrafluoroboric acid-diethyl ether results in the formation of diferrocenyl(hydroxy)cyclopropenylium tetrafluoroborate; nucleophiles, including methyllithium and lithium aluminum hydride, react regioselectively with the three-membered ring by opening it to form the respective substituted cis-diferrocenylethenes. We present data from X-ray diffraction analyses of 2,3-diferrocenylcyclopropenone, isopropyl cis-2,3-diferrocenylacrylate, and cis-3,4-diferrocenyl-2-methylbut-3-en-2-ol. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Klimova, E.I., Klimova Berestneva, T., Ruiz Ramirez, L., Cinquantini, A., Corsini, M., Zanello, P., et al. (2003). 2,3-Diferrocenylcyclopropenone: Synthesis, Structure, and Some Chemical and Electrochemical Properties. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003(21), 4265-4272 [10.1002/ejoc.200300318].
2,3-Diferrocenylcyclopropenone: Synthesis, Structure, and Some Chemical and Electrochemical Properties
Cinquantini A.;Corsini M.;Zanello P.;
2003-01-01
Abstract
Alkylation of ferrocene with tetrachlorocyclopropene in the presence of AlCl3 followed by aqueous workup affords 2,3-diferrocenylcyclopropenone in high yield. We have studied some of this ketone's chemical transformations and electrochemical properties. 2,3-Diferrocenylcyclopropenone withstands thermolysis; it is stable in an acidic medium; the action of tetrafluoroboric acid-diethyl ether results in the formation of diferrocenyl(hydroxy)cyclopropenylium tetrafluoroborate; nucleophiles, including methyllithium and lithium aluminum hydride, react regioselectively with the three-membered ring by opening it to form the respective substituted cis-diferrocenylethenes. We present data from X-ray diffraction analyses of 2,3-diferrocenylcyclopropenone, isopropyl cis-2,3-diferrocenylacrylate, and cis-3,4-diferrocenyl-2-methylbut-3-en-2-ol. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
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https://hdl.handle.net/11365/1143917
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