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Pure Appl. Chem., 1982, Vol. 54, No. 5, pp. 1015-1039

http://dx.doi.org/10.1351/pac198254051015

Recent advances in the chemistry of bridged annulenes

E. Vogel

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  • Yamada Michio, Akasaka Takeshi, Nagase Shigeru: Carbene Additions to Fullerenes. Chem. Rev. 2013, 113, 7209. <http://dx.doi.org/10.1021/cr3004955>
  • Lash Timothy D.: Carbaporphyrins, porphyrin isomers and the legacy of Emanuel Vogel. J. Porphyrins Phthalocyanines 2012, 16, 423. <http://dx.doi.org/10.1142/S1088424612300017>
  • Vogel Emanuel: Von kleinen Kohlenstoffringen zu Porphyrinen - ein persönlicher Bericht über 50 Jahre Forschung. Angew. Chem. 2011, 123, 4366. <http://dx.doi.org/10.1002/ange.201101347>
  • Altenbach Hans-Josef: Emanuel Vogel (1927-2011). angew chemie 2011, 123, 6833. <http://dx.doi.org/10.1002/ange.201103222>
  • Vogel Emanuel: From Small Carbocyclic Rings to Porphyrins: A Personal Account of 50 Years of Research. Angew. Chem. Int. Ed. 2011, 50, 4278. <http://dx.doi.org/10.1002/anie.201101347>
  • Altenbach Hans-Josef: Emanuel Vogel (1927-2011). Angew Chem Int E 2011, 50, 6701. <http://dx.doi.org/10.1002/anie.201103222>
  • Sun Yun-Shan, Ding Kai, Tian Wei-Sheng: Total syntheses of (Sp)-(+)- and (Rp)-(−)-spiniferin-1, a pair of unusual natural products with planar chirality. Chemical Communication 2011, 47, 10437. <http://dx.doi.org/10.1039/c1cc13650j>
  • Kuroda Shigeyasu, Oda Mitsunori, Tamura Naoko, Miyatake Ryuta, Matsumoto Naoko, Horino Yoshikazu, Miyawaki Daisuke: Synthesis and Emission Properties of 1,6-Methano[10]annulene-3,4-dicarboximides. HETEROCYCLES 2011, 83, 789. <http://dx.doi.org/10.3987/COM-11-12135>
  • Zhang Yanmei, Hisano Eri, Ohta Reina, Miyatake Ryuta, Horino Yoshikazu, Oda Mitsunori, Kuroda Shigeyasu: Discreteness of π-conjugation of 1,6-methano[10]annulene by troponoid fusion at the 3,4-positions. Tetrahetron Lett 2008, 49, 888. <http://dx.doi.org/10.1016/j.tetlet.2007.11.161>
  • Altenbach Hans-Josef, Blech Bernd, Marco Juan Alberto, Vogel Emanuel: 7-Azanorbornadien. Angew Chem 2006, 94, 789. <http://dx.doi.org/10.1002/ange.19820941017>
  • Hilken Günter, Kinkel Tonio, Schwamborn Michael, Lex Johann, Schmickler Hans, Vogel Emanuel: Tricarbonyl-2,7-methanoaza[10]annulenchrom(0). Angew Chem 2006, 94, 790. <http://dx.doi.org/10.1002/ange.19820941018>
  • Scholl Thomas, Lex Johann, Vogel Emanuel: Stereochemie der Bromierung von 1,6-Methano[10]annulen. Angew Chem 2006, 94, 924. <http://dx.doi.org/10.1002/ange.19820941214>
  • Kajioka Takanori, Ikai Masamichi, Fujikawa Hisayoshi, Taga Yasunori: Disubstituted 1,6-methano[10]annulene derivatives for use in organic light-emitting diodes. Tetrahedron 2004, 60, 6183. <http://dx.doi.org/10.1016/j.tet.2004.05.050>
  • Kuroda Shigeyasu, Oda Mitsunori, Zuo Shengli, Kanayama Kimiko, Shah Shaheen I.M, Furuta Shinji, Miyatake Ryuta, Kyogoku Mayumi: Generation and [4+2] cycloaddition of 1,6-methano[10]annulene-3,4-quinodimethane: a novel synthesis of dimethyl 1,6-methanobenzo[3,4-a][10]annulene-13,14-dicarboxylate. Tetrahetron Lett 2001, 42, 6345. <http://dx.doi.org/10.1016/S0040-4039(01)01277-1>
  • Kuroda Shigeyasu, Zuo Shengli, Oda Mitsunori, Fukuta Atsushi, Kajioka Takanori, Saito Toyohiko, Furuta Shinji, Tsukumo Hitoshi, Sano Kenji, Miyatake Ryuta: A Convenient Synthetic Method for Preparing 2,5-Disubstituted 1,6-Methano[10]annulenes from 1,6-Diacetylcyclohepta-1,3,5-triene. Bull Chem Soc Jpn 2000, 73, 1659. <http://dx.doi.org/10.1246/bcsj.73.1659>
  • Sokolov V. I.: Chemistry of fullerenes, novel allotropic modifications of carbon. Russ Chem Bull 1999, 48, 1197. <http://dx.doi.org/10.1007/BF02495277>
  • Moorhoff Cornelis M.: An unusual condensation of alkyl 3-oxo-4-(triphenylarsoranylidene)butanoate with aldehydes; synthesis of symmetrical substituted 1,3,5-cycloheptatrienes. Tetrahetron Lett 1997, 38, 4157. <http://dx.doi.org/10.1016/S0040-4039(97)00809-5>
  • Vogel Emanuel: Novel porphyrinoid macrocycles and their metal complexes. J Heterocyclic Chem 1996, 33, 1461. <http://dx.doi.org/10.1002/jhet.5570330505>
  • Averdung Johannes, Albrecht Evelyn, Lauterwein Jürgen, Luftmann Heinrich, Mattay Jochen, Mohn Holger, Müller Wolfgang H., Meer Hans-Ulrich Ter: Photoreaktionen mit Fulleren-C60 [3 + 2]-Photocycloaddition von 2,3-Diphenyl-2H-azirin. Chem Ber 1994, 127, 787. <http://dx.doi.org/10.1002/cber.19941270431>
  • Neidlein Richard, Gürtler Stephan, Krieger Claus: Chemische Reaktionen mitFischer-Carben-Komplexen des 1,6-Methano[10]annulens. HCA 1994, 77, 2303. <http://dx.doi.org/10.1002/hlca.19940770818>
  • Lu Jia-Xi, Chen Zhi-Da: Novel quasi-aromatic transition metal cluster compounds. Int Rev Phys Chem 1994, 13, 85. <http://dx.doi.org/10.1080/01442359409353291>
  • Belik Pavel, Gügel Andreas, Spickermann Jochen, Müllen Klaus: Umsetzung von Buckminsterfulleren C60 mitortho-Chinodimethan: ein neuer Zugang zu stabilen C60-Derivaten. Angew Chem 1993, 105, 95. <http://dx.doi.org/10.1002/ange.19931050121>
  • Belik Pavel, Gügel Andreas, Spickermann Jochen, Müllen Klaus: Reaction of Buckminsterfullerene withortho-Quinodimethane: a New Access to Stable C60 Derivatives. Angew Chem Int Ed Engl 1993, 32, 78. <http://dx.doi.org/10.1002/anie.199300781>
  • Isaacs Lyle, Wehrsig Arno, Diederich François: Improved Purification of C60 and Formation of σ- and π-Homoaromatic methano-bridged fullerenes by reaction with alkyl diazoacetates. HCA 1993, 76, 1231. <http://dx.doi.org/10.1002/hlca.19930760310>
  • Isaacs Lyle, Diederich François: Structures and Chemistry of Methanofullerenes: A Versatile Route intoN-[(Methanofullerene)carbonyl]-Substituted Amino Acids. HCA 1993, 76, 2454. <http://dx.doi.org/10.1002/hlca.19930760705>
  • Sokolov V. I.: The problem of fullerenes. The chemical aspect. Russ Chem Bull 1993, 42, 1. <http://dx.doi.org/10.1007/BF00699966>
  • Sokolov Vyacheslav I, Stankevich Ivan V: The fullerenes — new allotropic forms of carbon: molecular and electronic structure, and chemical properties. RUSS CHEM REV 1993, 62, 419. <http://dx.doi.org/10.1070/RC1993v062n05ABEH000025>
  • Higuchi Hiroyuki, Hashimoto Tamae, Nakafuku Kaori, Ojima Juro, Yamamoto Gaku: Synthesis, Structural and Conformational Analysis of Methanohomo(15)annulene and Methanohomo(19)annulene. Bull Chem Soc Jpn 1993, 66, 294. <http://dx.doi.org/10.1246/bcsj.66.294>
  • Diederich François, Rubin Yves, Diederich F., Rubin Y.: Strategien zum Aufbau molekularer und polymerer Kohlenstoffallotrope. Angew Chem 1992, 104, 1123. <http://dx.doi.org/10.1002/ange.19921040904>
  • Diederich François, Rubin Yves: Synthetic Approaches toward Molecular and Polymeric Carbon Allotropes. Angew Chem Int Ed Engl 1992, 31, 1101. <http://dx.doi.org/10.1002/anie.199211013>
  • Neidlein Richard, Schröder Günter: Reaktive 3,4-disubstituierte Derivate des 1,6-Methano[10]annulens und ihr Synthesepotential. Chem Ber 1992, 125, 2225. <http://dx.doi.org/10.1002/cber.19921251009>
  • Gupta Ashok K., Fu Xiaoyong, Snydert James P., Cook James M.: General approach for the synthesis of polyquinenes via the Weiss reaction. Tetrahedron 1991, 47, 3665. <http://dx.doi.org/10.1016/S0040-4020(01)80896-6>
  • Goldschmidt Zeev, Gottlieb Hugo E., Almadhoun Amira, Balci Metin, Demir Yasar: Activation of electron deficient cycloheptatrienes by tricarbonyliron complexation. Tetrahetron Lett 1990, 31, 6711. <http://dx.doi.org/10.1016/S0040-4039(00)97154-5>
  • Fabian Jürgen, Zahradník Rudolf: Auf der Suche nach tieffarbigen organischen Verbindungen. Angew Chem 1989, 101, 693. <http://dx.doi.org/10.1002/ange.19891010604>
  • Meyer Axel, Schlögl Karl, Lerch Ulrike, Vogel Emanuel: Stereochemistry of Planarchiral Compounds, 11. Static and dynamic stereochemistry of 10,10′-dibromo-2,2′-bi(1,6-methano[10]annulenyl). Chem Ber 1988, 121, 917. <http://dx.doi.org/10.1002/cber.19881210515>
  • Stowasser Bernd, Hafner Klaus: Synthese eines Dicyclopen[a,e]pentalens durch [6 + 2]-Cycloaddition von 1,3-Di-tert-butyl-5-vinylidencyclopentadien und konsekutive 8π-elektrocyclische Reaktion. Angew Chem 1986, 98, 477. <http://dx.doi.org/10.1002/ange.19860980533>
  • Ojima Juro, Ejiri Emiko, Kato Tadahito, Kuroda Shigeyasu, Hirooka Shuji, Shibutani Mitsuo: The synthesis of methano-bridged bisdehydro [18]-, -[20]-, -[22]-, and -[24] annulenes. Tetrahetron Lett 1986, 27, 2467. <http://dx.doi.org/10.1016/S0040-4039(00)84558-X>
  • Gerson Fabian, Knöbel Jürgen, Lopez Javier, Vogel Emmanuel: The Radical Anions ofsyn-1,6:8,13-Bridged [14] Annulenes. A Compilation of Hyperfine Data. HCA 1985, 68, 371. <http://dx.doi.org/10.1002/hlca.19850680211>
  • Jurić A., Sabljić A., Trinajstić N.: Aromaticity in bridged heteroannulenes. J Heterocyclic Chem 1984, 21, 273. <http://dx.doi.org/10.1002/jhet.5570210201>
  • Scholl Thomas, Lex Johann, Vogel Emanuel: Stereochemistry of the Bromination of 1,6-Methano[10]annulene. Angew Chem Int Ed Engl 1982, 21, 920. <http://dx.doi.org/10.1002/anie.198209201>
  • Hilken Günter, Kinkel Tonio, Schwamborn Michael, Lex Johann, Schmickler Hans, Vogel Emanuel: Tricarbonyl-2,7-methanoaza[10]annulenchrom(0). Angew Chem Int Ed Engl 1982, 21, 1622. <http://dx.doi.org/10.1002/anie.198216220>
  • Scholl Thomas, Lex Johann, Vogel Emanuel: Stereochemie der Bromierung von 1,6-Methano[10]annulen. Angew Chem Int Ed Engl 1982, 21, 1927. <http://dx.doi.org/10.1002/anie.198219270>