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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1745-1756

http://dx.doi.org/10.1351/pac200072091745

Bicyclopropylidene. A unique tetrasubstituted alkene and versatile C6-building block for organic synthesis

Gary A. Molander

Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany

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  • Wang Wei, Zhang Wen-Jie, Wang Lei, Quah Ching Kheng, Fun Hoong-Kun, Xu Jian-Hua, Zhang Yan: Photoinduced Reactions of para-Quinones with Bicyclopropylidene Leading to Diverse Polycyclic Compounds with Spirocyclopropanes. J. Org. Chem. 2013, 78, 6211. <http://dx.doi.org/10.1021/jo4008767>
  • Chen Gen-Qiang, Shi Min: Rhodium-catalyzed tandem Pauson–Khand type reactions of 1,4-enynes tethered by a cyclopropyl group. Chem. Commun. 2013, 49, 698. <http://dx.doi.org/10.1039/c2cc37587g>
  • Chen Kai, Sun Run, Xu Qin, Wei Yin, Shi Min: Thermal induced intramolecular [2 + 2] cycloaddition of allene-ACPs. Org. Biomol. Chem. 2013, 11, 3949. <http://dx.doi.org/10.1039/c3ob40911b>
  • Li Shaoyu, Li Zhiming, Wu Jie: Synthesis of Benzoindolines via a Copper-Catalyzed Reaction of 1-Bromoethynyl-2-(cyclopropylidenemethyl)arenes with N -Allylsulfonamide. Adv. Synth. Catal. 2012, 354, 3087. <http://dx.doi.org/10.1002/adsc.201200374>
  • Arndt Marion, Hilt Gerhard, Khlebnikov Alexander F., Kozhushkov Sergei I., de Meijere Armin: Diels-Alder Reactions for the Construction of Cyclopropylarenes. Eur J Org 2012, 2012, 3112. <http://dx.doi.org/10.1002/ejoc.201200105>
  • Chen Gen-Qiang, Tang Xiang-Ying, Shi Min: HOTf mediated cascade reactions of 1-arenoylcyclopropanecarboxylic acids with arenes. Chem Commn 2012, 48, 2340. <http://dx.doi.org/10.1039/c2cc17581a>
  • Chen Kai, Zhang Zhen, Wei Yin, Shi Min: Thermally induced [3+2] cyclization of aniline-tethered alkylidenecyclopropanes: a facile synthetic protocol of pyrrolo[1,2-a]indoles. Chem. Commun. 2012, 48, 7696. <http://dx.doi.org/10.1039/c2cc33269h>
  • Wu Dong-Dong, He Ming-Tao, Liu Qi-Di, Wang Wei, Zhou Jie, Wang Lei, Fun Hoong-Kun, Xu Jian-Hua, Zhang Yan: Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione. Biomol Chem 2012, 10, 3626. <http://dx.doi.org/10.1039/c2ob07158d>
  • Chen Kai, Jiang Min, Zhang Zhen, Wei Yin, Shi Min: Palladium(0)-Catalyzed Reaction of Cyclopropylidenecycloalkanes with Carbon Dioxide. Eur J Org 2011, 2011, 7189. <http://dx.doi.org/10.1002/ejoc.201101192>
  • Wu Lei, Shi Min: BF3·OEt2-catalyzed intermolecular reactions of arylmethylenecyclopropanes with (E)-1,1,3-triarylprop-2-en-1-ols. Tetrahedron 2011, 67, 5732. <http://dx.doi.org/10.1016/j.tet.2011.06.009>
  • Larina Anna G., Stepakov Alexander V., Boitsov Vitaly M., Molchanov Alexander P., Gurzhiy Vladislav V., Starova Galina L., Lykholay Anna N.: The first example of 1,3-dipolar cycloaddition reactions of nitrones to vinylidenecyclopropanes. Tet Letts 2011, 52, 5777. <http://dx.doi.org/10.1016/j.tetlet.2011.08.116>
  • Li Shaoyu, Luo Yong, Wu Jie: An Efficient Approach to Fused Indolines via a Copper(I)-Catalyzed Reaction of Sulfonyl Azide with 2-Ethynylaryl Methylenecyclopropane. Org Lett 2011, 13, 3190. <http://dx.doi.org/10.1021/ol2011067>
  • Hoyte Sarah A., Spencer John L.: Mono- and Diphosphine Platinum(0) Complexes of Methylenecyclopropane, Bicyclopropylidene, and Allylidenecyclopropane. Organomettalics 2011, 30, 5415. <http://dx.doi.org/10.1021/om200630z>
  • Inami Tasuku, Kurahashi Takuya, Matsubara Seijiro: Methylenecyclopropane as C1 synthetic units: [1+4] cycloaddition via a nickel catalyst. Chemical Communication 2011, 47, 9711. <http://dx.doi.org/10.1039/c1cc13540f>
  • Audran Gérard, Pellissier Hélène: Synthesis of Methylene- and Alkylidenecyclopropane Derivatives. Adv Synth Catal 2010, 352, 575. <http://dx.doi.org/10.1002/adsc.200900872>
  • Wu Lei, Shi Dr Min: Yb(OTf)3-Catalyzed Construction of Indole Derivatives through Formal [3+3] Cycloaddition of 1,1-Vinylidenecyclopropanediesters with Nitrones. Chem Eur J 2010, 16, 1149. <http://dx.doi.org/10.1002/chem.200902510>
  • De Meijere Armin, Kozhushkov Sergei I., Spath Thomas, Von Seebach Malte, Lohr Sandra, Nuske Hanno, Pohlmann Tim, Es-Sayed Mazen, Brase Stefan: ChemInform Abstract: Bicyclopropylidene: A Unique Tetrasubstituted Alkene and Versatile C6 Building Block for Organic Synthesis. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200126259>
  • Hu Bao, Jiang Linan, Ren Jun, Wang Zhongwen: A nBuLi-Mediated, Expeditious and Stereoselective Ring-Opening Rearrangement of (Arylmethylene)cyclopropane-1,1-dicarboxylates. Eur J Org Chem 2010, 2010, 1358. <http://dx.doi.org/10.1002/ejoc.200901165>
  • de Meijere Armin, Khlebnikov Alexander F., Sünnemann Hans Wolf, Frank Daniel, Rauch Karsten, Yufit Dmitrii S.: Convenient Access to Various 1-Cyclopropylcyclopropane Derivatives. Eur J Org 2010, 2010, 3295. <http://dx.doi.org/10.1002/ejoc.201000209>
  • Tang Xiang-Ying, Shi Min: HOTf-Catalyzed Rearrangement of Methylenecyclopropane Aryl and Alkyl Alcohols. Eur J Org Chem 2010, 2010, 4106. <http://dx.doi.org/10.1002/ejoc.201000509>
  • Shi Min, Zhang Di-Han, Dai Lun-Zhi: C(sp3)-C(sp3) Bond Breaking in Methylenecyclopropanes Involving a AuI/AuIII Catalytic Cycle. Eur J Org Chem 2010, 2010, 5454. <http://dx.doi.org/10.1002/ejoc.201000765>
  • Tang Xiang-Ying, Wei Yin, Shi Min: Ring-Opening Reaction of Methylenecyclopropanes Derived from Methylenecyclopropyl Aldehydes through Cope Rearrangement. Eur J Org Chem 2010, 2010, 6038. <http://dx.doi.org/10.1002/ejoc.201000880>
  • Hu Bao, Zhu Jianlin, Xing Siyang, Fang Jie, Du Ding, Wang Zhongwen: A Highly Site-, Regio-, and Stereoselective Lewis Acid Catalyzed Formal [3+3] Cycloaddition of Methylenecyclopropane-1,1-Diesters with C,N-Diarylnitrones. Chem. Eur. J. 2009, 15, 324. <http://dx.doi.org/10.1002/chem.200801990>
  • Bagutski Viktor, de Meijere Armin: Cyclopropyl Building Blocks for Organic Synthesis, 139. Ethyl Cyclopropylidenepyruvate as a Novel Multifunctional Cyclopropyl Building Block: Facile Preparation and Basic Reaction Patterns. Adv Synth Catal 2007, 349, 1247. <http://dx.doi.org/10.1002/adsc.200600617>
  • Kurahashi Takuya, Kozhushkov Sergei I., Schill Heiko, Meindl Kathrin, Rühl Stephan, de Meijere Armin: 1,1′-Verknüpfung von Cyclopropan-Derivaten: die helicale Konformation von Quinquecyclopropanol. Angew Chem 2007, 119, 6665. <http://dx.doi.org/10.1002/ange.200702013>
  • Kurahashi Takuya, Kozhushkov Sergei I., Schill Heiko, Meindl Kathrin, Rühl Stephan, de Meijere Armin: 1,1′-Linked Cyclopropane Derivatives: The Helical Conformation of Quinquecyclopropanol. Angew Chem Int Ed 2007, 46, 6545. <http://dx.doi.org/10.1002/anie.200702013>
  • von Seebach Malte, Kozhushkov Sergei I., Schill Heiko, Frank Daniel, Boese Roland, Benet-Buchholz Jordi, Yufit Dmitry S., de Meijere Armin: Stereoselective Preparation of Six Diastereomeric Quatercyclopropanes from Bicyclopropylidene and Some Derivatives. Chem Eur J 2007, 13, 167. <http://dx.doi.org/10.1002/chem.200600799>
  • Schill Heiko, Kozhushkov Sergei I., Walsh Robin, de Meijere Armin: The Thermal Transformations of Bicyclopropylidene and Methylenespiropentane Revisited. Eur J Org Chem 2007, 2007, 1510. <http://dx.doi.org/10.1002/ejoc.200601100>
  • de Meijere Armin, Khlebnikov Alexander F., Kozhushkov Sergei I., Yufit Dmitrii S., Chetina Olga V., Howard Judith A. K., Kurahashi Takuya, Miyazawa Kazutoshi, Frank Daniel, Schreiner Peter R.: Syntheses and Properties of Enantiomerically Pure Higher (n ≥ 7) [n−2]Triangulanedimethanols and σ-[n]Helicenes. Chem Eur J 2006, 12, 5697. <http://dx.doi.org/10.1002/chem.200600111>
  • Kozhushkov Sergei I., Foerstner Jan, Kakoschke Alf, Stellfeldt Dirk, Yong Li, Wartchow Rudolf, de Meijere Armin, Butenschön Holger: Syntheses and Structures of Sterically Congested Linear and Branched Cobalta[n]triangulanes. Chem Eur J 2006, 12, 5642. <http://dx.doi.org/10.1002/chem.200600118>
  • Zanobini Alessandra, Brandi Alberto, de Meijere Armin: A New Three-Component Cascade Reaction to Yield 3-Spirocyclopropanatedβ-Lactams. Eur J Org Chem 2006, 2006, 1251. <http://dx.doi.org/10.1002/ejoc.200500838>
  • Marradi Marco, Brandi Alberto, Magull Jörg, Schill Heiko, de Meijere Armin: New Highly Strained Multifunctional Heterocycles by Intramolecular Cycloadditions of Nitrones to Bicyclopropylidene Moieties. Eur J Org Chem 2006, 2006, 5485. <http://dx.doi.org/10.1002/ejoc.200600417>
  • de Meijere Armin, Becker Heike, Stolle Andreas, Kozhushkov Sergei I., Bes M. Teresa, Salaün Jacques, Noltemeyer Mathias: Intramolecular Pauson-Khand Reactions of Methylenecyclopropane and Bicyclopropylidene Derivatives as an Approach to Spiro(cyclopropanebicyclo[n.3.0]alkenones). Chem Eur J 2005, 11, 2471. <http://dx.doi.org/10.1002/chem.200400997>
  • de Meijere Armin, Kostikov Rafael R., Molchanov Alexander P., Diev Vyacheslav V., Magull Jörg, Vidović Denis, Kozhushkov Sergei I.: Carbonyl Ylide Cycloadditions to C,C-Double Bonds of Methylenecyclopropanes. Eur J Org Chem 2005, 2005, 593. <http://dx.doi.org/10.1002/ejoc.200400601>
  • Knoke Mario, de Meijere Armin: Domino Heck-Diels-Alder Reactions of Differently Substituted Cyclopropylallenes. Eur J Org Chem 2005, 2005, 2259. <http://dx.doi.org/10.1002/ejoc.200500024>
  • Schelper Michael, Buisine Olivier, Kozhushkov Sergei, Aubert Corinne, de Meijere Armin, Malacria Max: Cobalt(I)-Mediated Intramolecular [2+2+2] Cocyclizations of (Methylenecyclopropyl)diynes as an Easy Access to Cyclopropanated Oligocycles. Eur J Org Chem 2005, 2005, 3000. <http://dx.doi.org/10.1002/ejoc.200500111>
  • Yücel Baris, Arve Lars, de Meijere Armin: A two-step four-component queuing cascade involving a Heck coupling, π-allylpalladium trapping and Diels–Alder reaction. Tetrahedron 2005, 61, 11355. <http://dx.doi.org/10.1016/j.tet.2005.09.014>
  • de Meijere Armin, Khlebnikov Alexander F., Kozhushkov Sergei I., Miyazawa Kazutoshi, Frank Daniel, Schreiner Peter R., Rinderspacher B. Christopher, Yufit Dmitrii S., Howard Judith A. K.: Ein konvergenter Zugang zu enantiomerenreinen höheren [n−2]Triangulandimethanol-Derivaten und [n]Triangulanen (n≥7). Angew Chem 2004, 116, 6715. <http://dx.doi.org/10.1002/ange.200461166>
  • de Meijere Armin, Khlebnikov Alexander F., Kozhushkov Sergei I., Miyazawa Kazutoshi, Frank Daniel, Schreiner Peter R., Rinderspacher B. Christopher, Yufit Dmitrii S., Howard Judith A. K.: A Convergent Route to Enantiomerically Pure Higher [n−2]Triangulanedimethanol Derivatives and [n]Triangulanes (n≥7). Angew Chem Int Ed 2004, 43, 6553. <http://dx.doi.org/10.1002/anie.200461166>
  • de Meijere Armin, Schelper Michael, Knoke Mario, Yucel Baris, Sünnemann Hans Wolf, Scheurich René Peter, Arve Lars: Palladium-catalyzed cross-coupling reactions and electrocyclizations—efficient combinations for new cascade reactions. J Organomet Chem 2003, 687, 249. <http://dx.doi.org/10.1016/j.jorganchem.2003.07.007>
  • de Meijere Armin, Kozhushkov Sergei I., Boese Roland, Haumann Thomas, Yufit Dmitrii S., Howard Judith A. K., Khaikin Leonid S., Trætteberg Marit: Structural Parameters and Electronic Interactions in Substituted 1,1-Diethynylcyclopropanes − An Experimental Study. Eur J Org Chem 2002, 2002, 485. <http://dx.doi.org/10.1002/1099-0690(20022)2002:3<485::AID-EJOC485>3.0.CO;2-7>
  • de Meijere Armin, Khlebnikov Alexander F., Kozhushkov Sergei I., Kostikov Rafael R., Schreiner Peter R., Wittkopp Alexander, Rinderspacher Christopher, Menzel Henning, Yufit Dmitrii S., Howard Judith A. K.: The First Enantiomerically Pure [n]Triangulanes and Analogues: σ-[n]Helicenes with Remarkable Features. Chem Eur J 2002, 8, 828. <http://dx.doi.org/10.1002/1521-3765(20020215)8:4<828::AID-CHEM828>3.0.CO;2-Y>
  • de Meijere Armin, von Seebach Malte, Zöllner Stefan, Kozhushkov Sergei I., Belov Vladimir N., Boese Roland, Haumann Thomas, Benet-Buchholz Jordi, Yufit Dmitrii S., Howard Judith A. K.: Spirocyclopropanated Bicyclopropylidenes: Straightforward Preparation, Physical Properties, and Chemical Transformations. Chem Eur J 2001, 7, 4021. <http://dx.doi.org/10.1002/1521-3765(20010917)7:18<4021::AID-CHEM4021>3.0.CO;2-E>