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Pure Appl. Chem., 1995, Vol. 67, No. 5, pp. 673-682

http://dx.doi.org/10.1351/pac199567050673

Cyclic electron delocalization in hydrocarbon cages: Pagodanes, isopagodanes, (bisseco/seco-)dodecahedradienes

H. Prinzbach, G. Gescheidt, H.-D. Martin, R . Herges, J. Heinze, G. K. Surya Prakash and G. A. Olah

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  • Neshchadin Dmytro, Gescheidt Georg: CIDNP as a tool for rapid rearrangements: New insights into cyclobutanoid 4-center/3-electron radical cations. J. Phys. Org. Chem. 2013, 26, 737. <http://dx.doi.org/10.1002/poc.3153>
  • Shubina Tatyana E., Fokin Andrey A.: Hydrocarbon σ-radical cations. WIREs Comput Mol Sci 2011, 1, 661. <http://dx.doi.org/10.1002/wcms.24>
  • Mathew Thomas, Tonne Joern, Sedelmeier Gottfried, Grund Clemens, Keller Manfred, Hunkler Dieter, Knothe Lothar, Prinzbach Horst: [6+6]Photocycloadditions in Face-to-Face Benzo/Pyridazino Substrates – En Route to Azapagodanes. Eur J Org Chem 2007, 2007, 2133. <http://dx.doi.org/10.1002/ejoc.200601075>
  • Sackers Emmerich, Oßwald Thomas, Weber Klaus, Keller Manfred, Hunkler Dieter, Wörth Jürgen, Knothe Lothar, Prinzbach Horst: Bromination of Unsaturated Dodecahedranes—En Route to C20 Fullerene. Chem Eur J 2006, 12, 6242. <http://dx.doi.org/10.1002/chem.200501609>
  • Exner Kai, Heizmann Markus, Yang Fushun, Kegel Markus, Keller Manfred, Knothe Lothar, Großmann Birgit, Heinze Jürgen, Prinzbach Horst: Towards In-Plane Delocalized 4N/7e Radical Cations and 4N/6e Dications - One-/Two-Electron Oxidation of Proximate-Parallel Bis(N,N'-bicyclic)-bishydrazines. Eur J Org Chem 2005, 2005, 1311. <http://dx.doi.org/10.1002/ejoc.200400647>
  • Weber Klaus, Voss Thorsten, Heimbach Dirk, Weiler Andreas, Keller Manfred, Wörth Jürgen, Knothe Lothar, Exner Kai, Prinzbach Horst: From unsaturated dodecahedranes to C40 cages?. Tetrahetron Lett 2005, 46, 5471. <http://dx.doi.org/10.1016/j.tetlet.2005.06.072>
  • Qu Zheng-Wang, Zhu Hui, Zhang Xing-Kang, Zhang Qi-Yuan: Density functional investigation on electron-transfer catalysis of cycloreversion of cyclobutane: Radical anion mechanism. J Comput Chem 2003, 24, 340. <http://dx.doi.org/10.1002/jcc.10177>
  • Reinbold Jens, Sackers Emmerich, Oßwald Thomas, Weber Klaus, Weiler Andreas, Voss Torsten, Hunkler Dieter, Wörth Jürgen, Knothe Lothar, Sommer Frank: Unsaturated Dodecahedranes—In Quest of the C20H14 1,4,16-Triene and C20H12 1,4,10(14),16-Tetraene, and Their Cations and Anions. Chem Eur J 2002, 8, 509. <http://dx.doi.org/10.1002/1521-3765(20020118)8:2<509::AID-CHEM509>3.0.CO;2-D>
  • Qu Zheng-wang, Zhu Hui, Zhang Xiao-dong, Ai Xi-cheng, Zhang Jian-ping, Zhang Xing-kang, Zhang Qi-yuan: Density functional investigation on the cycloreversion of cyclobutane radical cation: new reaction mechanism. chem phys letts 2002, 360, 283. <http://dx.doi.org/10.1016/S0009-2614(02)00836-9>
  • Geier Jens, Exner Kai, Vögtle Markus, Kegel Markus, Yang Fushun, Hunkler Dieter, Cullmann Oliver, Prinzbach Horst: In-plane homoconjugation/homoaromaticity in preoriented 4N-anions—‘scope and limitations’. Tetrahedron 2002, 58, 1137. <http://dx.doi.org/10.1016/S0040-4020(01)01208-X>
  • Prinzbach Horst, Reinbold Jens, Bertau Martin, Voss Torsten, Martin Hans-Dieter, Mayer Bernhard, Heinze Jürgen, Neschchadin Dmytro, Gescheidt Georg, Prakash G. K. Surya: σ-Bishomokonjugation (σ-Bishomoaromatizität) in 4C/3(2)e-Kationen - Voraussetzungen und Grenzen. Angew Chem 2001, 113, 930. <http://dx.doi.org/10.1002/1521-3757(20010302)113:5<930::AID-ANGE930>3.0.CO;2-O>
  • Prinzbach Horst, Reinbold Jens, Bertau Martin, Voss Torsten, Martin Hans-Dieter, Mayer Bernhard, Heinze Jürgen, Neschchadin Dmytro, Gescheidt Georg, Prakash G. K. Surya: σ-Bishomoconjugation (σ-Bishomoaromaticity) in 4C/3(2)e Cations—Scope and Limitations. Angew Chem Int Ed 2001, 40, 911. <http://dx.doi.org/10.1002/1521-3773(20010302)40:5<911::AID-ANIE911>3.0.CO;2-B>
  • Kochi Jay K., Rathore Rajendra, Zhu, and Chengjian, Lindeman Sergey V.: Structural Characterization of Novel Olefinic Cation Radicals: X-ray Crystallographic Evidence of σ–π Hyperconjugation. Angew Chem 2000, 112, 3817. <http://dx.doi.org/10.1002/1521-3757(20001016)112:20<3817::AID-ANGE3817>3.0.CO;2-Q>
  • Kochi Jay K., Rathore Rajendra, Zhu, and Chengjian, Lindeman Sergey V.: Structural Characterization of Novel Olefinic Cation Radicals: X-ray Crystallographic Evidence of σ–π Hyperconjugation. Angew Chem 2000, 39, 3671. <http://dx.doi.org/10.1002/1521-3773(20001016)39:20<3671::AID-ANIE3671>3.0.CO;2-D>
  • Exner Kai, Fischer Gerhard, Lugan Meinrad, Fritz Hans, Hunkler Dieter, Keller Manfred, Knothe Lothar, Prinzbach Horst: Proximate,syn-Periplanar Diazene/Diazene(di)oxy, Diazeneoxy/Diazene(di)oxy, and Diazenedioxy/Diazenedioxy Skeletons: Syntheses, [2+2]Photocycloadditions, Metathesis. Eur J Org Chem 2000, 2000, 787. <http://dx.doi.org/10.1002/(SICI)1099-0690(200003)2000:5<787::AID-EJOC787>3.0.CO;2-N>
  • Exner Kai, Hunkler Dieter, Gescheidt Georg, Prinzbach Horst: Zur Existenz nichtklassischer, cyclisch delokalisierter 4N/5e-Radikalanionen und 4N/6e-Dianionen – Ein- und Zweielektronen-Reduktion nahgeordneter, synperiplanarer Bisdiazene. Angew Chem 1998, 110, 2013. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980703)110:13/14<2013::AID-ANGE2013>3.0.CO;2-M>
  • Camps Pelayo, Font-Bardia Mercè, Méndez Núria, Pérez Francesc, Pujol Xavier, Solans Xavier, Vázquez Santiago, Vilalta Montserrat: Highly pyramidalized tricyclo[3.3.0.03,7]oct-1(5)-ene and related compounds: High-level ab initio study, synthesis and trapping of tetracyclo[5.2.1.02,6.03,8] dec-7-ene, and cross-coupling reactions. Tetrahedron 1998, 54, 4679. <http://dx.doi.org/10.1016/S0040-4020(98)00185-9>
  • Pinkos Rolf, Weiler Andreas, Voss Torsten, Weber Klaus, Wahl Fabian, Melder Johann-Peter, Fritz Hans, Hunkler Dieter, Prinzbach Horst: From Pagodanes to Homologous, Non-Pentagonal Dodecahedranes. Liebigs Ann /Recueil 1997, 1997, 2069. <http://dx.doi.org/10.1002/jlac.199719971010>
  • Camps Pelayo, Pérez Francesc, Vázquez Santiago: Pentacyclo[8.2.1.12,5.14,7.18,11]hexadeca-1,7-diene and its 4,5,10,11-tetramethyl derivative, two highly hyperstable slightly pyramidalized dienes. Tetrahedron 1997, 53, 9727. <http://dx.doi.org/10.1016/S0040-4020(97)00595-4>
  • Exner Kai, Hochstrate Dirk, Keller Manfred, Klärner Frank-Gerrit, Prinzbach Horst: Nahgeordnete, synperiplanare Diazen/Diazen-Substrate; NN/NNO und ONN/NNO-Photometathese-Reaktionen. Angew Chem 1996, 108, 2399. <http://dx.doi.org/10.1002/ange.19961081929>
  • Sharma Veeraraghava, Keller Manfred, Weiler Andreas, Hunkler Dieter, Prinzbach Horst: Von Pagodanen zu nichtpentagonalen (Homo)Dodecahedranen – der Undecacyclo[10. 10.10.0.02, 20.03, 10.04, 19.05, 9.− 06, 18.07, 15.08, 13.019, 22.016, 21]docosan-Käfig. Angew Chem 1996, 108, 3029. <http://dx.doi.org/10.1002/ange.19961082338>
  • Bertau Martin, Leonhardt Jürgen, Weiler Andreas, Weber Klaus, Prinzbach Horst: The Pagodane → Dodecahedrane Concept–Shorter Routes, Higher Yields. Chem Eur J 1996, 2, 570. <http://dx.doi.org/10.1002/chem.19960020517>
  • Mathew Thomas, Keller Manfred, Hunkler Dieter, Prinzbach Horst: [6+6]-Photocycloadditions in “face-to-face” systems en route to azapagodanes (azadodecahedranes). Tetrahetron Lett 1996, 37, 4491. <http://dx.doi.org/10.1016/0040-4039(96)00895-7>
  • Melder Johann-Peter, Weber Klaus, Weiler Andreas, Sackers Emmerich, Fritz Hans, Hunkler Dieter, Prinzbach Horst: Unsaturated dodecahedranes—Synthesis of the highly pyramidalized, highly reactive C20H18 and C20H16 olefins. Res. Chem. Intermed. 1996, 22, 667. <http://dx.doi.org/10.1163/156856796X00142>
  • Martin Hans-Dieter, Mayer Bernhard, Weber Klaus, Wahl Fabian, Prinzbach Horst: PE-spectroscopic investigation of nonconjugated π,π interactions in (seco)dodecahedradienes — on the route to an experimental ethylene/ethylene cycloaddition reaction coordinate. Liebigs Ann /Recueil 1995, 1995, 2019. <http://dx.doi.org/10.1002/jlac.1995199511283>