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2,3‐Diferrocenylcyclopropenone: Synthesis, Structure, and Some Chemical and Electrochemical Properties
Author(s) -
Klimova Elena I.,
Klimova Berestneva Tatiana,
Ramirez Lena Ruiz,
Cinquantini Arnaldo,
Corsini Maddalena,
Zanello Piero,
HernándezOrtega Simón,
García Marcos Martínez
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300318
Subject(s) - chemistry , methyllithium , thermal decomposition , nucleophile , ferrocene , electrochemistry , alkylation , tetrafluoroborate , ketone , ether , aluminum hydride , lithium (medication) , diethyl ether , medicinal chemistry , hydride , aqueous solution , organic chemistry , ionic liquid , ion , hydrogen , medicine , methoxide , endocrinology , catalysis , electrode
Alkylation of ferrocene with tetrachlorocyclopropene in the presence of AlCl 3 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)