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Collect. Czech. Chem. Commun. 1997, 62, 1577-1584
https://doi.org/10.1135/cccc19971577

Synthesis of Triferrocenylbenzenes by Tantalum(V)-Catalyzed Cyclotrimerization of Ethynylferrocene. The Crystal Structure of 1,3,5-Triferrocenylbenzene

Petr Štěpničkaa, Ivana Císařováa, Jan Sedláčekb, Jiří Vohlídalb and Miroslav Polášekc

a Department of Inorganic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Department of Physical and Macromolecular Chemistry, Charles University, 128 40 Prague 2, Czech Republic
c J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 182 23 Prague 8, Czech Republic

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  • Harmach Petr, Baumann Benedikt N., Schulz Jiří, Císařová Ivana, Hapke Marko, Štěpnička Petr: Catalytic Synthesis and Cyclometalation of (4-Ferrocenylphenyl)pyridines. Organometallics 2024, 43, 1929. <https://doi.org/10.1021/acs.organomet.4c00284>
  • Misin Vyacheslav M., Maltseva Irina E., Kazakov Mark E., Volkov Vladimir A.: The Polymers of Diethynylarenes—Is Selective Polymerization at One Acetylene Bond Possible? A Review. Polymers 2023, 15, 1105. <https://doi.org/10.3390/polym15051105>
  • McGlinchey Michael J.: Ferrocenyl Migrations and Molecular Rearrangements: The Significance of Electronic Charge Delocalization. Inorganics 2020, 8, 68. <https://doi.org/10.3390/inorganics8120068>
  • Sekerová Lada, Vyskočilová Eliška, Červený Libor, Sedláček Jan: A novel application of terminal alkynes as the homogeneous catalysts for acetalization and esterification. Tetrahedron 2019, 75, 2877. <https://doi.org/10.1016/j.tet.2019.04.013>
  • Sedláček Jan, Sokol Jiří, Zedník Jiří, Faukner Tomáš, Kubů Martin, Brus Jiří, Trhlíková Olga: Homo‐ and Copolycyclotrimerization of Aromatic Internal Diynes Catalyzed with Co2(CO)8: A Facile Route to Microporous Photoluminescent Polyphenylenes with Hyperbranched or Crosslinked Architecture. Macromol. Rapid Commun. 2018, 39. <https://doi.org/10.1002/marc.201700518>
  • Xie Rui-Jun, Han Li-Min, Zhu Ning, Gao Yuan-Yuan, Hong Hai-Long, Suo Quan-Ling: Synthesis of tetraferrocenylbenzene by cycloaddition reaction with alkyl cobalt clusters as reaction precursors. Journal of Coordination Chemistry 2015, 68, 449. <https://doi.org/10.1080/00958972.2014.997720>
  • Korotvička Aleš, Šnajdr Ivan, Štěpnička Petr, Císařová Ivana, Janoušek Zbyněk, Kotora Martin: Synthesis, Molecular Structure, and Electrochemistry of 1‐Ferrocenyl‐1,2‐dicarba‐closo‐dodecaboranes. Eur J Inorg Chem 2013, 2013, 2789. <https://doi.org/10.1002/ejic.201300110>
  • Zukal Arnošt, Slováková Eva, Balcar Hynek, Sedláček Jan: Polycyclotrimers of 1,4‐Diethynylbenzene, 2,6‐Diethynylnaphthalene, and 2,6‐Diethynylanthracene: Preparation and Gas Adsorption Properties. Macro Chemistry & Physics 2013, 214, 2016. <https://doi.org/10.1002/macp.201300317>
  • Korotvička Aleš, Císařová Ivana, Roithová Jana, Kotora  Martin: Synthesis of Aromatic Compounds by Catalytic CC Bond Activation of Biphenylene or Angular [3]Phenylene. Chemistry A European J 2012, 18, 4200. <https://doi.org/10.1002/chem.201103888>
  • Pfaff Ulrike, Hildebrandt Alexander, Schaarschmidt Dieter, Hahn Torsten, Liebing Simon, Kortus Jens, Lang Heinrich: Di- and Triferrocenyl (Hetero)Aromatics: Synthesis, Characterization, (Spectro-)Electrochemistry, and Calculations. Organometallics 2012, 31, 6761. <https://doi.org/10.1021/om300511v>
  • Xie Rui-Jun, Han Li-Min, Gao Yuan-Yuan, Zhu Ning, Hong Hai-Long, Suo Quan-Ling: An effective method for the synthesis of monoferrocenylbenzene derivatives. Journal of Coordination Chemistry 2012, 65, 4086. <https://doi.org/10.1080/00958972.2012.732696>
  • Tauchman Jiří, Carvalho M. Fernanda N. N., Štěpnička Petr: Selective hydration of ferrocenylethyne mediated by a palladium complex with a camphorhydrazone ligand. Collect. Czech. Chem. Commun. 2011, 76, 1277. <https://doi.org/10.1135/cccc2011130>
  • Xu Bao‐Hua, Peng Xu‐Qing, Li Yi‐Zhi, Yan Hong: Reactions of 16e CpCo Half‐Sandwich Complexes Containing a Chelating 1,2‐Dicarba‐closo‐dodecaborane‐1,2‐dichalcogenolate Ligand with Ethynylferrocene and Dimethyl Acetylenedicarboxylate. Chemistry A European J 2008, 14, 9347. <https://doi.org/10.1002/chem.200801136>
  • Steffens Stefan, Prosenc Marc H., Heck Jürgen, Asselberghs Inge, Clays Koen: Trigonal‐Pyramidal Tetra‐Sandwich Complexes as 3D NLOphores. Eur J Inorg Chem 2008, 2008, 1999. <https://doi.org/10.1002/ejic.200701267>
  • Balcar Hynek, Topka Pavel, Sedláček Jan, Zedník Jiří, Čejka Jiří: Polymerization of aliphatic alkynes with heterogeneous Mo catalysts supported on mesoporous molecular sieves. J. Polym. Sci. A Polym. Chem. 2008, 46, 2593. <https://doi.org/10.1002/pola.22600>
  • Wang Michael C.P., Li Yunchao, Merbouh Nabyl, Yu Hua-Zhong: Thin-layer electrochemistry of ferrocenylbenzene derivatives: Intramolecular electronic communication. Electrochimica Acta 2008, 53, 7720. <https://doi.org/10.1016/j.electacta.2008.05.043>
  • Ogini Francis O., Ortin Yanick, Mahmoudkhani Amir H., Cozzolino Anthony F., McGlinchey Michael J., Vargas-Baca Ignacio: An investigation of the formation of 1,3,5-heterosubstituted benzene rings by cyclo-condensation of acetyl-substituted organometallic complexes. Journal of Organometallic Chemistry 2008, 693, 1957. <https://doi.org/10.1016/j.jorganchem.2008.02.013>
  • Doležal Zdeněk, Kubinec Róbert, Sedláček Jan, Pacáková Vera, Vohlídal Jirí: Characterization of substituted polyacetylene microstructure by pyrolysis gas chromatography. J of Separation Science 2007, 30, 731. <https://doi.org/10.1002/jssc.200600388>
  • Mathur Pradeep, Chatterjee Saurav, Das Atanu, Mobin Shaikh M.: Photochemical route to unusual tri-tungsten ferrocenylacetylene cluster [W3{μ-η2,η2- (H)CCFc}2(CO)12] and a dimetallacyclodecatetraene [W2{μ-η2,η2,η2,η2- (Fc)CC(H)C(H)C(Fc)C(Fc)C(H)C(H)C(Fc)}(CO)6]. Journal of Organometallic Chemistry 2007, 692, 819. <https://doi.org/10.1016/j.jorganchem.2006.10.022>
  • Lim Young-Kwan, Wallace Scott, Bollinger John C., Chen Xufang, Lee Dongwhan: Triferrocenes Built on a C3-Symmetric Ligand Platform:  Entry to Redox-Active pseudo-Triphenylenes via Chelation-Driven Stereoselection of Triple Schiff Bases. Inorg. Chem. 2007, 46, 1694. <https://doi.org/10.1021/ic062029v>
  • Fiorentini Simone, Floris Barbara, Galloni Pierluca, Grepioni Fabrizia, Polito Mauro, Tagliatesta Pietro: The Metal‐Catalyzed Cyclotrimerization of Ferrocenylethyne – Preparation and Characterization of 1,2,4‐Triferrocenylbenzene. Eur J Org Chem 2006, 2006, 1726. <https://doi.org/10.1002/ejoc.200500896>
  • Li Yunchao, Tsang Emily M.W., Chan Andy Y.C., Yu Hua-Zhong: Thin-layer electrochemistry of 1,3,5-triferrocenylbenzene: A unique two-step, three-electron redox process. Electrochemistry Communications 2006, 8, 951. <https://doi.org/10.1016/j.elecom.2006.04.001>
  • Mathur Pradeep, Singh Amrendra K., Singh Vinay K., Singh Priti, Rahul, Mobin Shaikh M., Thöne Carsten: Coupling Reactions of Ferrocenylacetylene with Mononuclear Metal Carbonyls Fe(CO)5 and M(CO)6 (M = Mo, W):  Synthesis and Characterization of [Fe(CO)2{η5-2,5-Fc2C5H2CO}C(Fc)CH], [Fe(CO)2{η2:η2-2,5-Fc2C4H2Fe(CO)3}-μ-CO], [Fe(CO)3{η2:η2-2,5-Fc2C4H2CO}], 1,2,4-Triferrocenylbenzene, 2,5-Diferrocenylthiophene, and 2,5-Diferrocenylselenophene. Organometallics 2005, 24, 4793. <https://doi.org/10.1021/om0504755>
  • Dufková Lenka, Matsumura Hiroshi, Nečas David, Štěpnička Petr, Uhlík Filip, Kotora Martin: Reaction of Zirconacyclopentadienes with Ethynylferrocenes. Collect. Czech. Chem. Commun. 2004, 69, 351. <https://doi.org/10.1135/cccc20040351>
  • Dufková Lenka, Císařová Ivana, Štepnička Petr, Kotora Martin: [2+2+2] Cocyclotrimerization with Ferrocenylalkynes. Eur J Org Chem 2003, 2003, 2882. <https://doi.org/10.1002/ejoc.200300119>
  • Stará Irena G., Starý Ivo, Kollárovič Adrian, Teplý Filip, Šaman David, Fiedler Pavel: Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes. Collect. Czech. Chem. Commun. 2003, 68, 917. <https://doi.org/10.1135/cccc20030917>
  • Mertis Konstantinos, Arbilias Stavros, Argyris Demos, Psaroudakis Nikos, Vohlídal Jiří, Lavastre Olivier, Dixneuf Pierre H.: First Examples of Homogeneous Catalytic Cyclotrimerization and Polymerization of Phenylacetylene and Copolymerization of Phenylacetylene and Norbonene with Dinuclear Complexes Containing Unbridged Metal-Metal Quadruple Bond. Collect. Czech. Chem. Commun. 2003, 68, 1094. <https://doi.org/10.1135/cccc20031094>
  • Ma Kuangbiao, Lerner Hans-Wolfram, Scholz Stefan, Bats Jan W, Bolte Michael, Wagner Matthias: Stepwise assembly and structural characterization of oligonuclear ferrocene aggregates with boron–nitrogen backbone. Journal of Organometallic Chemistry 2002, 664, 94. <https://doi.org/10.1016/S0022-328X(02)01968-X>
  • Hocek Michal, Stará Irena G., Starý Ivo, Dvořáková Hana: Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil. Collect. Czech. Chem. Commun. 2002, 67, 1223. <https://doi.org/10.1135/cccc20021223>
  • Gupta Hari K, Reginato Nada, Ogini Francis O, Brydges Stacey, McGlinchey Michael J: SiCl4–ethanol as a trimerization agent for organometallics: convenient syntheses of the symmetrically substituted arenes 1,3,5-C6H3R3 where R = (C5H4)Mn(CO)3 and (C5H4)Fe(C5H5). Can. J. Chem. 2002, 80, 1546. <https://doi.org/10.1139/v02-152>
  • Štěpnička Petr, Trojan Libor, Kubišta Jiřı́, Ludvı́k Jiřı́: Internal ferrocenylalkynes—a comparative electrochemical and mass spectrometric study. Journal of Organometallic Chemistry 2001, 637-639, 291. <https://doi.org/10.1016/S0022-328X(01)00922-6>
  • Hocek Michal, Stará Irena G, Starý Ivo, Dvořáková Hana: Cyclotrimerization of 6-ethynylpurines. Synthesis of 1,2,4- and 1,3,5-tris(purin-6-yl)benzenes as novel Hoogsteen-triplet analogues. Tetrahedron Letters 2001, 42, 519. <https://doi.org/10.1016/S0040-4039(00)01989-4>
  • Štĕpnička Petr, Podlaha Jaroslav, Horáček Michal, Hanuš Vladimı́r, Mach Karel: A directly ring-to-ring linked ferrocene–pseudotitanocene complex. Journal of Organometallic Chemistry 1999, 580, 210. <https://doi.org/10.1016/S0022-328X(98)01147-4>