Pure Appl. Chem., 1971, Vol. 25, No. 3, pp. 573-622
http://dx.doi.org/10.1351/pac197125030573
Conformational mobility and fast bond shift in the annulenes
CrossRef Cited-by Linking
- An Ke, Zhu Jun: Evaluation of Triplet Aromaticity by the Indene-Isoindene Isomerization Stabilization Energy Method. Eur. J. Org. Chem. 2014, n/a. <http://dx.doi.org/10.1002/ejoc.201301810>
- Schild Axel, Paulus Beate: Multireference calculations for ring inversion and double bond shifting in cyclooctatetraene. J. Comput. Chem. 2013, 34, 1393. <http://dx.doi.org/10.1002/jcc.23273>
- Sánchez-Sanz Goar, Trujillo Cristina, Rozas Isabel, Elguero José: A theoretical study on the aromaticity of benzene and related derivatives incorporating a C–CC–C fragment. Tetrahedron 2013, 69, 7333. <http://dx.doi.org/10.1016/j.tet.2013.06.072>
- Sokolov Alexander Yu., Magers D. Brandon, Wu Judy I., Allen Wesley D., Schleyer Paul v. R., Schaefer Henry F.: Free Cyclooctatetraene Dianion: Planarity, Aromaticity, and Theoretical Challenges. J. Chem. Theory Comput. 2013, 9, 4436. <http://dx.doi.org/10.1021/ct400642y>
- Wu Judy I., Fernández Israel, Schleyer Paul v. R.: Description of Aromaticity in Porphyrinoids. J. Am. Chem. Soc. 2013, 135, 315. <http://dx.doi.org/10.1021/ja309434t>
- Santander Mitchell V., Pastor Michael B., Nelson Jordan N., Castro Claire, Karney William L.: Hückel and Möbius Bond-Shifting Routes to Configuration Change in Dehydro[4n+2]annulenes. J. Org. Chem. 2013, 78, 2033. <http://dx.doi.org/10.1021/jo302072p>
- Mouri Kazuhiro, Saito Shohei, Hisaki Ichiro, Yamaguchi Shigehiro: Thermal 8π electrocyclic reaction of heteroarene tetramers: new efficient access to π-extended cyclooctatetraenes. Chem. Sci. 2013, 4, 4465. <http://dx.doi.org/10.1039/c3sc52232f>
- Mouri Kazuhiro, Saito Shohei, Yamaguchi Shigehiro: Highly Flexible π-Expanded Cyclooctatetraenes: Cyclic Thiazole Tetramers with Head-to-Tail Connection. Angew. Chem. 2012, 124, 6073. <http://dx.doi.org/10.1002/ange.201201265>
- Mouri Kazuhiro, Saito Shohei, Yamaguchi Shigehiro: Highly Flexible π-Expanded Cyclooctatetraenes: Cyclic Thiazole Tetramers with Head-to-Tail Connection. Angew. Chem. Int. Ed. 2012, 51, 5971. <http://dx.doi.org/10.1002/anie.201201265>
- Castro Claire, Karney William L.: Mechanisms and Möbius strips: understanding dynamic processes in annulenes. J. Phys. Org. Chem. 2012, 25, 612. <http://dx.doi.org/10.1002/poc.2904>
- Hudson Bruce S., Allis Damian G.: The structure of [18]-annulene: Computed Raman spectra, zero-point level and proton NMR chemical shifts. Journal of Molecular Structure 2012, 1023, 212. <http://dx.doi.org/10.1016/j.molstruc.2012.05.016>
- Wu Judy I., Fernández Israel, Mo Yirong, Schleyer Paul von Ragué: Why Cyclooctatetraene Is Highly Stabilized: The Importance of “Two-Way” (Double) Hyperconjugation. J Chem Theory and Comput 2012, 8, 1280. <http://dx.doi.org/10.1021/ct3000553>
- Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure-Eight-Strukturen, Möbius-Bänder und mehr: Konformation und Aromatizität von Porphyrinoiden. Angew. Chem. 2011, 123, 4376. <http://dx.doi.org/10.1002/ange.201003353>
- Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids. Angew. Chem. Int. Ed. 2011, 50, 4288. <http://dx.doi.org/10.1002/anie.201003353>
- Pacholska-Dudziak Ewa, Szterenberg Ludmiła, Latos-Grażyński Lechosław: A Flexible Porphyrin-Annulene Hybrid: A Nonporphyrin Conformation formeso-Tetraaryldivacataporphyrin. Chem Eur J 2011, 17, 3500. <http://dx.doi.org/10.1002/chem.201002765>
- Borden Weston Thatcher: With a Little Help from My Friends: Forty Years of Fruitful Chemical Collaborations. J Org Chem 2011, 76, 2943. <http://dx.doi.org/10.1021/jo200213x>
- Thatcher Borden Weston, Carl Lineberger W.: The synergy between qualitative theory, quantitative calculations, and direct experiments in understanding, calculating, and measuring the energy differences between the lowest singlet and triplet states of organic diradicals. Phys Chem Chem Phys 2011, 13, 11792. <http://dx.doi.org/10.1039/c0cp02786c>
- Verbruggen A.: Ring Current and Aromaticity in Annulenes. Bull Soc Chim Belges 2010, 91, 865. <http://dx.doi.org/10.1002/bscb.19820911009>
- Hege Hans-Christian, Manz Jörn, Marquardt Falko, Paulus Beate, Schild Axel: Electron flux during pericyclic reactions in the tunneling limit: Quantum simulation for cyclooctatetraene. Chemical Phys 2010, 376, 46. <http://dx.doi.org/10.1016/j.chemphys.2010.07.033>
- Wannere Chaitanya S., Rzepa Henry S., Rinderspacher B. Christopher, Paul Ankan, Allan Charlotte S. M., Schaefer Henry F., Schleyer Paul v. R.: The Geometry and Electronic Topology of Higher-Order Charged Möbius Annulenes†. J Phys Chem A 2009, 113, 11619. <http://dx.doi.org/10.1021/jp902176a>
- Yoon Zin Seok, Osuka Atsuhiro, Kim Dongho: Möbius aromaticity and antiaromaticity in expanded porphyrins. Nature Chem 2009, 1, 113. <http://dx.doi.org/10.1038/nchem.172>
- Mauksch Michael, Tsogoeva Svetlana B.: Neutral Möbius Aromatics: Derivatives of the Pyrrole Congener Aza[11]annulene as Promising Synthetic Targets. Eur J Org Chem 2008, 2008, 5755. <http://dx.doi.org/10.1002/ejoc.200800815>
- Kleinpeter Erich, Klod Sabrina, Koch Andreas: Visualization of through space NMR shieldings of aromatic and anti-aromatic molecules and a simple means to compare and estimate aromaticity. Journal of Molecular Structure: THEOCHEM 2007, 811, 45. <http://dx.doi.org/10.1016/j.theochem.2007.02.049>
- Wannere Chaitanya S., Moran Damian, Allinger Norman L., Hess, B. Andes, Schaad Lawrence J., Schleyer Paul von Ragué: On the Stability of Large [4n]Annulenes. Org Lett 2003, 5, 2983. <http://dx.doi.org/10.1021/ol034979f>
- Krygowski Tadeusz M., Pindelska Edyta, Cyrański Michał K., Häfelinger Günter: Planarization of 1,3,5,7-cyclooctatetraene as a result of a partial rehybridization at carbon atoms: an MP2/6-31 and B3LYP/6-311 study. chem phys letts 2002, 359, 158. <http://dx.doi.org/10.1016/S0009-2614(02)00681-4>
- Klärner Frank-Gerrit: Wie antiaromatisch ist planares Cyclooctatetraen?. Angew Chem 2001, 113, 4099. <http://dx.doi.org/10.1002/1521-3757(20011105)113:21<4099::AID-ANGE4099>3.0.CO;2-1>
- Quast Helmut, Heubes Markus, Dietz Thomas, Witzel Alexander, Boenke Martin, Roth Wolfgang R.: Thermal Isomerisation of Substituted Semibullvalenes and Cyclooctatetraenes – A Kinetic Study. Eur J Org Chem 1999, 1999, 813. <http://dx.doi.org/10.1002/(SICI)1099-0690(199904)1999:4<813::AID-EJOC813>3.0.CO;2-V>
- Märkl Gottfried, Sauer Heinrich, Kreitmeier Peter, Burgemeister Thomas, Kastner Fritz: Synthese von diepoxy[16]annulen(6.2) durch intramolekulare McMurry-Kupplung. Tetrahedron 1999, 55, 13407. <http://dx.doi.org/10.1016/S0040-4020(99)00825-X>
- Märkl Gottfried, Ehrl Robert, Kreitmeier Peter, Burgemeister Thomas: 8,19-Dimethyl-tetraepoxy[22]annulen(2.1.2.1): ein erstes Tetraepoxy-Verbrücktes aromatisches [22]Annulen. HCA 1998, 81, 93. <http://dx.doi.org/10.1002/hlca.19980810111>
- Märkl Gottfried, Sauer Heinrich, Stiegler Jürgen, Kreitmeier Peter, Burgemeister Thomas: Tetraepoxy[22]annulen(2.2.2.0): Ein neuartiges Tetraepoxy-verbrücktes, neutrales, aromatisches [22]Annulen. HCA 1998, 81, 1077. <http://dx.doi.org/10.1002/hlca.19980810521>
- Baumann Harold, Oth Jean F. M.: The Low-Temperature UV/VIS Absorption Spectrum of [14]Annulene. HCA 1995, 78, 679. <http://dx.doi.org/10.1002/hlca.19950780315>
- Minyaev Ruslan M: Gradient lines on multidimensional potential energy surfaces and chemical reaction mechanisms. RUSS CHEM REV 1994, 63, 883. <http://dx.doi.org/10.1070/RC1994v063n11ABEH000124>
- Pohl Michael, Schmickler Hans, Lex Johann, Vogel Emanuel: Isophlorine: Moleküle am Schnittpunkt von Porphyrin- und Annulen-Chemie. Angew Chem 1991, 103, 1737. <http://dx.doi.org/10.1002/ange.19911031248>
- Vogel Emanuel, Jux Norbert, Rodriguez-Val Eduardo, Lex Johann, Schmickler Hans: Die Porphyrin-Homologen: [22]Porphyrin (2.2.2.2), ein „gestrecktes Porphycen”. Angew Chem 1990, 102, 1431. <http://dx.doi.org/10.1002/ange.19901021206>
- Müllen Klaus, Heinz Willi, Klärner Frank-Gerrit, Roth Wolfgang R., Kindermann Islinde, Adamczak Oliver, Wette Michael, Lex Johann: InversionsbarrierenOrtho,ortho′-verbrückter Biphenyle. Chem Ber 1990, 123, 2349. <http://dx.doi.org/10.1002/cber.19901231219>
- Fabian Jürgen, Zahradník Rudolf: Auf der Suche nach tieffarbigen organischen Verbindungen. Angew Chem 1989, 101, 693. <http://dx.doi.org/10.1002/ange.19891010604>
- Wang Ting-Zhong, Paquette Leo A.: A convenient route to 1,3-cyclooctatetraenophanes. Tetrahetron Lett 1988, 29, 41. <http://dx.doi.org/10.1016/0040-4039(88)80011-X>
- Müllen Klaus: Neue reduktive Umwandlungen cyclischer ungesättigter Kohlenwasserstoffe. Angew Chem 1987, 99, 192. <http://dx.doi.org/10.1002/ange.19870990306>
- Müllen Klaus, Allison Neil T., Lex Johann, Schmickler Hans, Vogel Emanuel: Structure and fluxional behaviour of heptaleneirontricarbonyl and heptalenebis (Irontricarbonyl). Tetrahedron 1987, 43, 3225. <http://dx.doi.org/10.1016/S0040-4020(01)90290-X>
- Paquette Leo A., Trova Michael P.: Belting of the cyclooctatetraene ring across the transannular 1- and 5-positions. Tetrahetron Lett 1987, 28, 2795. <http://dx.doi.org/10.1016/S0040-4039(00)96211-7>
- Hafner Klaus, Knaup Günter L., Lindner Hans Jörg: Synthese und dynamische Eigenschaften substituierter Cyclohepta[ef]heptalene. Angew Chem 1986, 98, 650. <http://dx.doi.org/10.1002/ange.19860980722>
- Roth Wolfgang R., Lennartz Hans-Werner, Vogel Emanuel, Leiendecker Markus, Oda Masaji: Hydrierwärmen, 6. Resonanzenergie kondensierter [4n]Annulene. Chem Ber 1986, 119, 837. <http://dx.doi.org/10.1002/cber.19861190307>
- Paquette Leo A, Trova Michael P: An optically active cyclooctatetraene incapable of racemization. Tetrahetron Lett 1986, 27, 1895. <http://dx.doi.org/10.1016/S0040-4039(00)84404-4>
- Sundahl Mikael, Wennerström Olof, Sandros Kjell, Norinder Ulf: A sixfold triplet-sensitized Z/E isomerization of a π-perimeter macrocycle. Tetrahetron Lett 1986, 27, 1063. <http://dx.doi.org/10.1016/S0040-4039(86)80048-X>
- Hafner Klaus, Knaup Günter L., Lindner Hans Jörg, Flöter Hans-Christian: Synthese und dynamische Eigenschaften chiraler Heptalene. Angew Chem 1985, 97, 209. <http://dx.doi.org/10.1002/ange.19850970311>
- Hafner Klaus, Knaup Günter L., Lindner Hans Jörg, Flöter Hans-Christian: Synthesis and Dynamic Properties of Chiral Heptalenes. Angew Chem Int Ed Engl 1985, 24, 212. <http://dx.doi.org/10.1002/anie.198502121>
- Flitsch Wilhelm, Schulz Dieter, Kneip Heinz-Gerd: Verbindungen mit verminderten Porphin-π-Systemen: Synthese des 12,13,17,18-Tetranorporphins, der Stammverbindung der Isobakteriochlorine. Liebigs Ann Chem 1985, 1985, 1004. <http://dx.doi.org/10.1002/jlac.198519850514>
- 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>
- Vogel Emanuel, Engels Hans-Wilhelm, Matsumoto Saichi, Lex Johann: Benz[c]octalen. Tetrahetron Lett 1982, 23, 1797. <http://dx.doi.org/10.1016/S0040-4039(00)86744-1>
- Kaminski Victor V., Swenton John S., Cottrell Charles E.: Specific rearrangements of dihydropyrimidinediones to pyridones via diazacyclooctatetraene intermediates. Tetrahetron Lett 1982, 23, 4207. <http://dx.doi.org/10.1016/S0040-4039(00)88705-5>
- Binsch Gerhard, Kessler Horst: Die kinetische und mechanistische Auswertung von NMR-Spektren. Neue analytische Methoden (18). Angew Chem 1980, 92, 445. <http://dx.doi.org/10.1002/ange.19800920606>
- Binsch Gerhard, Kessler Horst: The Kinetic and Mechanistic Evaluation of NMR Spectra. New analytical methods (18). Angew Chem Int Ed Engl 1980, 19, 411. <http://dx.doi.org/10.1002/anie.198004113>
- Oth Jean F. M., Müllen Klaus, Schmickler Hans, Engels Hans-Wilhelm, Vogel Emanuel: π-Bond Configurations, Conformations, and Dynamic Behaviour of Benzo[c]octalene and Dibenzo[c,j]octalene. HCA 1980, 63, 2411. <http://dx.doi.org/10.1002/hlca.19800630834>
- Günther Harald, Günther Maria-Eugenia, Mondeshka Diana, Schmickler Hans, Sondheimer Franz, Darby Nicolas, Cresp Terry M.: Protonenresonanz-Spektroskopie ungesättigter Ringsysteme, XXVII. Der Benzolkern als Sonde für die π-Elektronenstruktur von Annulenen; Teil IV: Dehydrobenzoannulene. Chem Ber 1979, 112, 71. <http://dx.doi.org/10.1002/cber.19791120107>
- Staab Heinz A., Meissner Ute E., Weinacht Wolfgang, Gensler Annelies: Konjugation in makrocyclischen Bindungssystemen, XXVIII. Benzo-anellierte [14]Annulene. Chem Ber 1979, 112, 3895. <http://dx.doi.org/10.1002/cber.19791121214>
- Boche Gernot, Weber Heinrich, Martens Dieter, Bieberbach Andreas: Darstellung descis,cis,cis,trans-[9]Annulen-Anions. Chem Ber 1978, 111, 2480. <http://dx.doi.org/10.1002/cber.19781110703>
- Boche Gernot, Weber Heinrich, Bieberbach Andreas: Topomerisierung descis,cis,cis,trans-[9]Annulen-Anions. Chem Ber 1978, 111, 2833. <http://dx.doi.org/10.1002/cber.19781110810>
- Boche Gernot, Bieberbach Andreas: Isomerisierung descis,cis,cis,trans-[9]Annulen-Anions. Chem Ber 1978, 111, 2850. <http://dx.doi.org/10.1002/cber.19781110811>
- Müllen Klaus: The Dianions of Pyrene and Pyrene Isomers as (4n)π-Perimeters. HCA 1978, 61, 2307. <http://dx.doi.org/10.1002/hlca.19780610704>
- Oth Jean F. M., Müllen Klaus, Runzheimer Hans-Volker, Mues Peter, Vogel Emanuel: Konfiguration, Konformation und Dynamik von Octalen. Angew Chem 1977, 89, 910. <http://dx.doi.org/10.1002/ange.19770891227>
- Gygax Ruedi, Wirz Jakob, Sprague Joseph T., Allinger Norman L.: Conjugative Stabilization in an “Antiaromatic” System: The Conformational Mobility of 1,5-Bisdehydro[12]annulene. HCA 1977, 60, 2522. <http://dx.doi.org/10.1002/hlca.19770600805>
- Hellwinkel Dieter, Reiff Günther, Nykodym Vaclav: Verbrückte Tetraphenylen-Systeme. Justus Liebigs Ann Chem 1977, 1977, 1013. <http://dx.doi.org/10.1002/jlac.197719770615>
- Wild Urs P., Griesser Hans J., Tuan Vo Dinh, Oth Jean F.M.: Fluorescence from the second excited singlet state of [18] annulenes. chem phys letts 1976, 41, 450. <http://dx.doi.org/10.1016/0009-2614(76)85391-2>
- Figeys H.P., Defay N., Martin R.H., McOmie J.F.W., Ayres B.E., Chadwick J.B.: Experimental and theoretical study of the induced paramagnetic ring-current in the 4-membered ring of biphenylene and related hydrocarbons. Tetrahedron 1976, 32, 2571. <http://dx.doi.org/10.1016/0040-4020(76)88029-5>
- Boche Gernot, Bieberbach Andreas: Isomerization of the ,,,-[9]annulene anion. Tetrahetron Lett 1976, 17, 1021. <http://dx.doi.org/10.1016/S0040-4039(00)77995-0>
- Boche Gernot, Bieberbach Andreas, Weber Heinrich: Die Topomerisierung descis, cis, cis, trans-[9]Annulen-Anions. Angew Chem 1975, 87, 550. <http://dx.doi.org/10.1002/ange.19750871515>
- Boche Gernot, Bieberbach Andreas, Weber Heinrich: Topomerization of thecis,cis,cis,trans-[9]Annulene Anion. Angew Chem Int Ed Engl 1975, 14, 562. <http://dx.doi.org/10.1002/anie.197505621>
- Paquette Leo A.: The renaissance in cyclooctatetraene chemistry. Tetrahedron 1975, 31, 2855. <http://dx.doi.org/10.1016/0040-4020(75)80303-6>
- Ege G., Vogler H.: Zur konjugation in makrocyclischen bindungssystemen—V. Tetrahedron 1975, 31, 569. <http://dx.doi.org/10.1016/0040-4020(75)85031-9>
- Vogel Emanuel, Königshofen Heinrich, Müllen Klaus, Oth Jean F. M.: 1,7-Methano-[12]annulen — das 12π-Analogon des 1,6-Methano-[10]annulens. Angew Chem 1974, 86, 229. <http://dx.doi.org/10.1002/ange.19740860604>
- Vogel Emanuel, Mann Max, Sakata Yoshiteru, Müllen Klaus, Oth Jean F. M.: 1,6-Methano-[12]annulen. Angew Chem 1974, 86, 231. <http://dx.doi.org/10.1002/ange.19740860605>
- Vogel Emanuel, Königshofen Heinrich, Wassen Jürgen, Müllen Klaus, Oth Jean F. M.: Heptalen-Synthese aus 1,6-Methano-[10]annulen; Nachweis einer schnellen π-Bindungsverschiebung. Angew Chem 1974, 86, 777. <http://dx.doi.org/10.1002/ange.19740862106>
- Vogel Emanuel, Königshofen Heinrich, Müllen Klaus, Oth Jean F. M.: 1,7-Methano[12]annulene—the 12π Analog of 1,6-Methano[10]annulene. Angew Chem Int Ed Engl 1974, 13, 281. <http://dx.doi.org/10.1002/anie.197402811>
- Vogel Emanuel, Mann Max, Sakata Yoshiteru, Müllen Klaus, Oth Jean F. M.: 1,6-Methano[12]annulene. Angew Chem Int Ed Engl 1974, 13, 283. <http://dx.doi.org/10.1002/anie.197402831>
- Vogel Emanuel, Königshofen Heinrich, Wassen Jürgen, Müllen Klaus, Oth Jean F. M.: A Heptalene Synthesis from 1,6-Methano[10]annulene; Evidence for a Fast π-Bond Shift. Angew Chem Int Ed Engl 1974, 13, 732. <http://dx.doi.org/10.1002/anie.197407321>
- Schröder Gerhard, Kirsch Gerald, Oth Jean F. M.: Monosubstituierte [16] Annulene. Chem Ber 1974, 107, 460. <http://dx.doi.org/10.1002/cber.19741070211>
- Oth Jean F. M., Müllen Klaus, Gilles Jean-Marie, Schröder Gerhard: Comparison of13C- and1H-Magnetic Resonance Spectroscopy as Techniques for the Quantitative Investigation of Dynamic Processes. The cope rearrangement in bullvalene. HCA 1974, 57, 1415. <http://dx.doi.org/10.1002/hlca.19740570518>
- Schröder Gerhard, Plinke Günter, Oth Jean F. M.: Oxa[17]annulene. Angew Chem 1972, 84, 472. <http://dx.doi.org/10.1002/ange.19720841006>
- Schröder Gerhard, Plinke Günter, Oth Jean F. M.: Oxa[17]annulenes. Angew Chem Int Ed Engl 1972, 11, 424. <http://dx.doi.org/10.1002/anie.197204241>