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Pure Appl. Chem., 1969, Vol. 20, No. 3, pp. 237-262

http://dx.doi.org/10.1351/pac196920030237

Perspektiven der Cycloheptatrien-Norcaradien-Valenztautomerie

Emanuel Vogel

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  • Gatti Carlo: Challenging chemical concepts through charge density of molecules and crystals. Phys. Scr. 2013, 87, 048102. <http://dx.doi.org/10.1088/0031-8949/87/04/048102>
  • Beniazza Redouane, Desvergnes Valérie, Girard Emeline, Kauffmann Brice, Berlande Muriel, Landais Yannick: Development of Domino Processes by Using 7-Silylcycloheptatrienes and Its Analogues. Chem. Eur. J. 2012, 18, 11976. <http://dx.doi.org/10.1002/chem.201201527>
  • 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>
  • Cerfontain Hans, Koeberg-Telder Ankie, Lerch Ulrike: Electrophilic substitution of two monohomoperylenes and perylene. Recl Trav Chim Pays-Bas 2010, 112, 584. <http://dx.doi.org/10.1002/recl.19931121105>
  • Kuroda Shigeyasu, Hirano Isao, Zhang Yanmei, Thanh Nguyen Chung, Oda Mitsunori: Synthesis, structure and some reactions of a multi-bridged unsaturated cyclooctadecane derivative formally having two cycloheptatrienes. Tet Letts 2007, 48, 5811. <http://dx.doi.org/10.1016/j.tetlet.2007.06.096>
  • Cremer Dieter, Dick Bernhard: Theoretische Untersuchungen zur Valenztautomerie zwischen 1,6-Methano[10]annulen und Tricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraen. Angew Chem 2006, 94, 877. <http://dx.doi.org/10.1002/ange.19820941126>
  • Vogel Emanuel, Scholl Thomas, Lex Johann, Hohlneicher Georg: Norcaradien-Valenztautomer eines 1,6-Methano[10]annulens: Tricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraen-11,11-dicarbonitril. Angew Chem 2006, 94, 878. <http://dx.doi.org/10.1002/ange.19820941127>
  • Mues Peter, Benn Reinhard, Krüger Carl, Tsay Yi-Hung, Vogel Emanuel, Wilke Günther: Erste Metallkomplexe der Norcaradienform von 1,6-Methano[10]annulen. Angew Chem 2006, 94, 879. <http://dx.doi.org/10.1002/ange.19820941128>
  • Laue Jörg, Seitz Gunther: Inverse and Normal [4 + 2] Cycloadditions of a 4a,8a-Methanophthalazine to Azirines and 1,2,4-Triazoline-3,5-dione as Heterodienophiles. Liebigs Ann /Recueil 2006, 1996, 645. <http://dx.doi.org/10.1002/jlac.199619960427>
  • Laue Jörg, Seitz Gunther: [4 + 2] Cycloaddition Reactions of a 4a,8a-Methanophthalazine with Electron-Rich Alkynes: A New Synthesis of Substituted 1,6-Methano[10]annulenes. Liebigs Ann /Recueil 2006, 1996, 773. <http://dx.doi.org/10.1002/jlac.199619960521>
  • Kassaee M.Z., Arshadi S., Haerizade B.N., Vessally E.: Electronic effects on 1H-azepines valance tautomerization: an ab initio comparative study. Journal of Molecular Structure: THEOCHEM 2005, 731, 29. <http://dx.doi.org/10.1016/j.theochem.2005.02.087>
  • Mealli Carlo, Ienco Andrea, Zoellner Robert W., Hoyt Earle B.: A Comprehensive Qualitative and Quantitative Molecular Orbital Analysis of the Factors Governing the Dichotomy in the Dinorcaradiene 1,6-Methano[10]annulene system. Chem Eur J 1997, 3, 958. <http://dx.doi.org/10.1002/chem.19970030618>
  • Schick Georg, Hirsch Andreas, Mauser Harald, Clark Timothy: Opening and Closure of the Fullerene Cage incis-Bisimino Adducts of C60: The Influence of the Addition Pattern and the Addend. Chem Eur J 1996, 2, 935. <http://dx.doi.org/10.1002/chem.19960020807>
  • Kohmoto Shigeo, Nakayama Naohiro, Takami Jun-ichi, Kishikawa Keiki, Yamamoto Makoto, Yamada Kazutoshi: On the mechanism of the rearrangement of 7-vinylnorcaradienes. Tetrahetron Lett 1996, 37, 7761. <http://dx.doi.org/10.1016/0040-4039(96)01771-6>
  • Anderson Harry L., Boudon Corinne, Diederich Francois, Gisselbrecht Jean-Paul, Gross Maurice, Seiler Paul: 61,61-Bis(trimethylsilylbutadiinyl)-1,2-dihydro-1,2-methanofulleren[60]: Kristallstruktur bei 100 K und elektrochemische Umwandlung in ein leitfähiges Polymer. Angew Chem 1994, 106, 1691. <http://dx.doi.org/10.1002/ange.19941061524>
  • 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>
  • Neidlein Richard, Kux Ulrich: Ein neues 1,6-Methano[10]annulen-Derivat mit Bisnorcaradien-Struktur – Synthesen mit Übergangsmetallkomplexen. Angew Chem 1993, 105, 1381. <http://dx.doi.org/10.1002/ange.19931050921>
  • Neidlein Richard, Kux Ulrich: A Novel 1,6-Methano[10]annulene Derivative with Bisnorcaradiene Structure—Syntheses with Transition Metal Complexes. Angew Chem Int Ed Engl 1993, 32, 1324. <http://dx.doi.org/10.1002/anie.199313241>
  • 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>
  • Raghavachari Krishnan, Sosa Carlos: Fullerene derivatives. Comparative theoretical study of C60O and C60CH2. chem phys letts 1993, 209, 223. <http://dx.doi.org/10.1016/0009-2614(93)80097-9>
  • Roth Wolfgang R., Klärner Frank-Gerrit, Siepert Gerd, Lennartz Hans-Werner: Hydrierwärmen, IV. Zur Frage der Homoaromatizität von Norcaradien und Cycloheptatrien. Chem Ber 1992, 125, 217. <http://dx.doi.org/10.1002/cber.19921250134>
  • Raghavachari Krishnan, McMichael Rohlfing Celeste: Ground state of C70O: oxygen bridging at the equatorial belt. chem phys letts 1992, 197, 495. <http://dx.doi.org/10.1016/0009-2614(92)85806-L>
  • Raghavachari Krishnan: Structure of C60O: unexpected ground state geometry. chem phys letts 1992, 195, 221. <http://dx.doi.org/10.1016/0009-2614(92)86139-9>
  • Sugihara Yoshikazu, Kanemaru Jun-ichi, Saito Junji, Murata Ichiro: A Novel Rearrangement in the Sterically Congested(2,4,6-Cycloheptatrienyl)(phenylsuflinyl)methyl Group. Chem Lett 1992, 2393. <http://dx.doi.org/10.1246/cl.1992.2393>
  • Arnz Roland, de M. Carneiro José Walkimar, Klug Wolfgang, Schmickler Hans, Vogel Emanuel, Breuckmann Rolf, Klärner Frank-Gerrit: σ-Homoacenaphthylen und π-Homoacenaphthen. Angew Chem 1991, 103, 702. <http://dx.doi.org/10.1002/ange.19911030614>
  • Alberto Marco J., Sanz Juan F., Vogel Emanuel, Schwartzkopff-Fischer Barbara, Schmickler Hans, Lex Johann: syn-1,6-imino-8,13-oxido[14]annulene. Tetrahetron Lett 1990, 31, 999. <http://dx.doi.org/10.1016/S0040-4039(00)94413-7>
  • Neidlein Richard, Bronner Patricia: Synthese und chemische Eigenschaften neuer 3,4-disubstituierter Tricyclo[4.4.1.01,6]undec-8-ene. Vorstufen für neue substituierte 1,6-Methano[10]annulene. Chem Ber 1989, 122, 1499. <http://dx.doi.org/10.1002/cber.19891220822>
  • Lange Walter, Tückmantel Werner: Synthesis and reactions of oligomethylene-clamped 1H-azepines and benzene imines. Their valence tautomeric equilibrium and nitrogen stereochemistry. Chem Ber 1989, 122, 1765. <http://dx.doi.org/10.1002/cber.19891220924>
  • Barzaghi Mario, Gatti Carlo: Substituent effect on the planarization energy and the relative stability of Winstein and M��bius structures of the homotropylium cation. Journal of Molecular Structure: THEOCHEM 1988, 167, 275. <http://dx.doi.org/10.1016/0166-1280(88)80232-X>
  • Haddon R.C.: Rehybridization and the Chemical Reaction: POAV and 3D-HMO Analysis. Tetrahedron 1988, 44, 7611. <http://dx.doi.org/10.1016/S0040-4020(01)86253-0>
  • Kawase Takeshi, Iyoda Masahiko, Oda Masaji: Synthese von Tricyclo[5.2.0.01,3]nona-4,6,8-trien, einem durch die Antiaromatizität von Cyclobutadien erzwungenen Norcaradien. Angew Chem 1987, 99, 574. <http://dx.doi.org/10.1002/ange.19870990616>
  • Cremer Dieter, Thiel Walter: On the importance of size-consistency corrections in semiempirical MNDOC calculations. J Comput Chem 1987, 8, 48. <http://dx.doi.org/10.1002/jcc.540080106>
  • My Nguyen Kieu, Schwarz Helmut: On the unimolecular loss of acetylene from metastable C11H9]+ ions. Org Mass Spectrom 1987, 22, 248. <http://dx.doi.org/10.1002/oms.1210220504>
  • Bianchi R., Gavezzotti A., Simonetta M., Huzinaga S., Klobukowski M., Rao C.N.R., Hegde M.S., Kamath P.V.: Molecular shape and crystal packing analysis of 11,11-disubstituted 1,6-methano[10]annulenes. Journal of Molecular Structure: THEOCHEM 1986, 135, 391. <http://dx.doi.org/10.1016/0166-1280(86)80071-9>
  • Simonetta M., Barzaghi M., Gatti C., Chiodini L., Malatesta V., Fusco R., Ranghino G., Scordamaglia R., Tosi C.: World congress of theoretical organic chemists. Journal of Molecular Structure: THEOCHEM 1986, 138, 247. <http://dx.doi.org/10.1016/0166-1280(86)87005-1>
  • Boger Dale L., Brotherton Christine E.: Diels-alder cycloaddition reactions of cyclopropenone ketals. Tetrahedron 1986, 42, 2777. <http://dx.doi.org/10.1016/S0040-4020(01)90567-8>
  • Huber Walter: Electron-Transfer-Induced Conformational Changes. The Example of 1,8-Dimethyl[14]annulene. HCA 1984, 67, 1368. <http://dx.doi.org/10.1002/hlca.19840670523>
  • Barzaghi M., Bianchi R., Gatti C., Simonetta M.: The ring closure reaction in 1,6-methano-[10]annulene. Int J Quantum Chem 1984, 26, 433. <http://dx.doi.org/10.1002/qua.560260839>
  • Dürr Heinz, Pauly Karl-Heinz, Fischer Karl: Ein Beitrag zum Bisnorcaradien-Problem. Synthese, Eigenschaften und Strukturparameter von Bicyclo[5.4.0]undecapentaen, dem Valenzisomer des Bisnorcaradiens. Chem Ber 1983, 116, 2855. <http://dx.doi.org/10.1002/cber.19831160812>
  • Neidlein Richard, Martin Radke Christoph: Untersuchungen an einem bei Raumtemperatur beobachtbaren langsamen Cycloheptatrien-Norcaradien-Gleichgewicht. HCA 1983, 66, 2626. <http://dx.doi.org/10.1002/hlca.19830660830>
  • Cremer Dieter, Dick Bernhard: Theoretical Investigations on the Valence Tautomerism between 1,6-Methanol[10]annulene and Tricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraene. Angew Chem Int Ed Engl 1982, 21, 865. <http://dx.doi.org/10.1002/anie.198208651>
  • Mues Peter, Benn Reinhard, Krüger Carl, Tsay Yi-Hung, Vogel Emanuel, Wilke Günther: First Metal Complexes of the Norcaradiene Form of 1,6-Methano[10]annulene. Angew Chem Int Ed Engl 1982, 21, 868. <http://dx.doi.org/10.1002/anie.198208681>
  • Vogel Emanuel, Scholl Thomas, Lex Johann, Hohlneicher Georg: Norcaradiene Valence Tautomer of a 1,6-Methanol[10]annulene: Tricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraene-11,11-dicarbonitrile. Angew Chem Int Ed Engl 1982, 21, 869. <http://dx.doi.org/10.1002/anie.198208691>
  • Vogel Emanuel, Scholl Thomas, Lex Johann, Hohlneicher Georg: Norcaradien-Valenztautomer eines 1,6-Methano[10]annulens: Tricyclo[4.4.1.0.1,6]undeca-2,4,7,9-tetraen-11,11-dicarbonitril. Angew Chem Int Ed Engl 1982, 21, 1882. <http://dx.doi.org/10.1002/anie.198218820>
  • Mues Peter, Benn Reinhard, Krüger Carl, Tsay Yi-Hung, Wilke Günther, Vogel E.: Erste Metallkomplexe der Norcaradienform von 1,6-Methano[10]annulen. Angew Chem Int Ed Engl 1982, 21, 1891. <http://dx.doi.org/10.1002/anie.198218910>
  • Budzikiewicz H., Roth G., Vogel E.: Massenspektroskopische Fragmentierungsreaktionen. XX—Zur Frage der elektronenstoß-induzierten Carbenabspaltung. Org Mass Spectrom 1979, 14, 140. <http://dx.doi.org/10.1002/oms.1210140307>
  • Gerson Fabian, Huber Walter, Müllen Klaus: Die Berson-Willcott-Umlagerung des 11,11-Dimethyltricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraens und seines Radikal-Anions. Angew Chem 1978, 90, 216. <http://dx.doi.org/10.1002/ange.19780900319>
  • Gavezzotti Angelo, Simonetta Massimo: ExtendedHückel Molecular Orbital Calculations for the Bridged Annulenes. HCA 1976, 59, 2984. <http://dx.doi.org/10.1002/hlca.19760590837>
  • Pauly Karl-Heinz, Dürr Heinz: Bisnorcaradiene - Synthesis and reactions - the first stable bisnorcaradiene. Tetrahetron Lett 1976, 17, 3649. <http://dx.doi.org/10.1016/S0040-4039(00)92984-8>
  • Filippini Giuseppe, Gramaccioli Carlo M., Simonetta Massimo, Suffritti Giuseppe B.: Thermal parameters of 11,11-dimethyltricyclo [4,4,1,01,6] undeca-2,4,7,9-tetraene: A lattice-dynamical discussion. chem phys letts 1974, 26, 301. <http://dx.doi.org/10.1016/0009-2614(74)85420-5>
  • Paquette Leo A.: NEW DELIGHTS FROM AN OLD POLYOLEFIN: A RETURN TO THE CHEMISTRY OF CYCLOOCTATETRAENE*. Transactions of the New York Academy of Sciences 1974, 36, 357. <http://dx.doi.org/10.1111/j.2164-0947.1974.tb01586.x>
  • Günther Harald, Schmickler Hans, Bremser Wolfgang, Straube Franz A., Vogel Emanuel: Ein Aromat-Olefin-Gleichgewicht: 1,6-Methano-[10]annulen-Tricyclo[4.4.1.0.1,6]-undeca-2,4,7,9-tetraen-Valenztautomerie. Angew Chem 1973, 85, 585. <http://dx.doi.org/10.1002/ange.19730851308>
  • Günther Harald, Schmickler Hans, Bremser Wolfgang, Straube Franz A., Vogel Emanuel: An Aromatic-Olefin Equilibrium: 1,6-Methano[10]annulene-Tricyclo[4.4.l.01,6]undeca-2,4,7,9-Tetraene Valence Tautomerism. Angew Chem Int Ed Engl 1973, 12, 570. <http://dx.doi.org/10.1002/anie.197305701>
  • Vogel Emanuel, Wiedemann Wolfgang, Roth Heinz Dieter, Eimer Johannes, Günther Harald: Ein Beitrag zum Norcaradien- Cycloheptatrien-Strukturproblem. Justus Liebigs Ann Chem 1972, 759, 1. <http://dx.doi.org/10.1002/jlac.19727590102>
  • Haddon R.C.: The application of the Biot-Savart law to the ring current analysis of proton chemical shifts—II. Tetrahedron 1972, 28, 3635. <http://dx.doi.org/10.1016/S0040-4020(01)93811-6>
  • Hoffmann Reinhard W.: Carbene durch thermische Cycloeliminierung. Angew Chem 1971, 83, 595. <http://dx.doi.org/10.1002/ange.19710831602>
  • Hoffmann Reinhard W.: Generation of Carbenes by Thermal Cycloelimination. Angew Chem Int Ed Engl 1971, 10, 529. <http://dx.doi.org/10.1002/anie.197105291>
  • Günther Harold, Keller Toni: Anwendungen der13C-Resonanz–Spektroskopie, I. Die Fourier-Transform-Spektren von Cycloheptatrienen und Norcaradienen. Chem Ber 1970, 103, 3231. <http://dx.doi.org/10.1002/cber.19701031027>