2,3-Diferrocenylcyclopropenone: Synthesis, Structure, and Some Chemical and Electrochemical Properties

• Published in: European journal of organic chemistry Vol. 2003; no. 21; pp. 4265 - 4272
• Main Authors: Klimova, Elena I., Klimova Berestneva, Tatiana, Ramirez, Lena Ruiz, Cinquantini, Arnaldo, Corsini, Maddalena, Zanello, Piero, Hernández-Ortega, Simón, García, Marcos Martínez
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.11.2003; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Organic; Cyclopropene; Electrochemistry; Ferrocene; Physical Sciences; Ring opening; Science & Technology; ring opening; FERROCENYL COMPOUNDS; electrochemistry; RING; BEHAVIOR; DIPHENYLCYCLOPROPENONE; ferrocene; cyclopropene
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200300318

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)