Isolation of Bicyclopropenylidenes: Derivatives of the Smallest Member of the Fulvalene Family
2008; Wiley; Volume: 121; Issue: 3 Linguagem: Inglês
10.1002/ange.200804372
ISSN1521-3757
AutoresRei Kinjo, Yutaka Ishida, B. Donnadieu, Guy Bertrand,
Tópico(s)Synthesis and Reactivity of Heterocycles
ResumoAngewandte ChemieVolume 121, Issue 3 p. 525-528 Zuschrift Isolation of Bicyclopropenylidenes: Derivatives of the Smallest Member of the Fulvalene Family† Rei Kinjo Dr., Rei Kinjo Dr. UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorYutaka Ishida Dr., Yutaka Ishida Dr. UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorBruno Donnadieu, Bruno Donnadieu UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGuy Bertrand Prof., Guy Bertrand Prof. [email protected] UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this author Rei Kinjo Dr., Rei Kinjo Dr. UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorYutaka Ishida Dr., Yutaka Ishida Dr. UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorBruno Donnadieu, Bruno Donnadieu UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGuy Bertrand Prof., Guy Bertrand Prof. [email protected] UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this author First published: 29 December 2008 https://doi.org/10.1002/ange.200804372Citations: 7 † Financial support from the NSF (CHE 0808825) is gratefully acknowledged. We also thank the JSPS for Fellowships (R.K. and Y.I.) and Dr. J. C. Daran for his help with the crystallographic part of this manuscript. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Unbegrenzt stabil ist ein Triafulvalenderivat unter Inertatmosphäre bei Raumtemperatur sowohl in Lösung als auch im Festkörper. Die Verbindung wurde durch eine magnesiumkatalysierte Kupplung von zwei Bis(chlorcyclopropenyl)-Derivaten synthetisiert. Ihre beiden ungesättigten Dreiringe sind über eine 1.303 Å lange, reaktive Kohlenstoff-Kohlenstoff-Doppelbindung verknüpft (siehe Struktur), die bei Raumtemperatur spontan Wasser addiert. Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description ange_200804372_sm_miscellaneous_information.pdf632.1 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1R. D. Brown, Trans. Faraday Soc. 1949, 45, 296–300. 10.1039/tf9494500296 CASWeb of Science®Google Scholar 2 2aC. Courtot, Ann. Chim. 1915, 4, 157–224; Web of Science®Google Scholar 2bC. Courtot, Ann. Chim. 1916, 5, 52–108. CASGoogle Scholar 3Although the compound was prepared by Courtot, its structure was ascertained in 1971: H. Prinzbach, Pure Appl. Chem. 1971, 28, 281–329. 10.1351/pac197128020281 CASGoogle Scholar 4E. C. Schreiber, E. I. Becker, J. Am. Chem. Soc. 1954, 76, 6125–6127. 10.1021/ja01652a078 Web of Science®Google Scholar 5N. Ueno, I. Murata, Y. Kitahara, Tetrahedron Lett. 1965, 6, 2967–2970. 10.1016/S0040-4039(01)89242-X Google Scholar 6For recent reviews on fulvalenes, see: B. Halton, Eur. J. Org. Chem. 2005, 3391–3414; 10.1002/ejoc.200500231 CASWeb of Science®Google ScholarH. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000. Google Scholar 7For recent reviews on tetrathiafulvalenes, see: Google Scholar 7aM. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891–4945; 10.1021/cr030666m CASPubMedWeb of Science®Google Scholar 7bA. Gorgues, P. Hudhomme, M. Sallé, Chem. Rev. 2004, 104, 5151–5184; See also: 10.1021/cr0306485 CASPubMedWeb of Science®Google ScholarP. Batail, Chem. Rev. 2004, 104, 4887–4890. 10.1021/cr040697x CASWeb of Science®Google Scholar 8 8aA. P. Scott, I. Agranat, P. U. Biedermann, N. V. Riggs, L. Radom, J. Org. Chem. 1997, 62, 2026–2038; 10.1021/jo962407l CASPubMedWeb of Science®Google Scholar 8bC. Läng, M. Mühlebach, M. Neuenschwander, Helv. Chim. Acta 1997, 80, 2124–2136; 10.1002/hlca.19970800712 CASWeb of Science®Google Scholar 8cY. Apeloig, R. Boese, B. Halton, A. H. Maulitz, J. Am. Chem. Soc. 1998, 120, 10147–10153; 10.1021/ja973020i CASWeb of Science®Google Scholar 8dR. F. Langler, Aust. J. Chem. 2001, 54, 51–57; 10.1071/CH00095 CASWeb of Science®Google Scholar 8eH. Möllerstedt, M. C. Piqueras, R. Crespo, H. Ottosson, J. Am. Chem. Soc. 2004, 126, 13938–13939; 10.1021/ja045729c CASPubMedWeb of Science®Google Scholar 8fG. Ghigo, A. R. M. Shahi, L. Gagliardi, L. M. Solstad, C. J. Cramer, J. Org. Chem. 2007, 72, 2823–2831; 10.1021/jo062420y CASPubMedWeb of Science®Google Scholar 8gM. M. Montero-Campillo, J. Rodriguez-Otero, E. M. Cabaleiro-Lago, J. Mol. Model. 2007, 13, 919–926; 10.1007/s00894-007-0211-x CASPubMedWeb of Science®Google Scholar 8hE. Kleinpeter, A. Holzberger, P. Wacker, J. Org. Chem. 2008, 73, 56–65. 10.1021/jo701520j CASPubMedWeb of Science®Google Scholar 9R. Neidlein, V. Poignée, W. Kramer, C. Glück, Angew. Chem. 1986, 98, 735–736; 10.1002/ange.19860980818 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1986, 25, 731–732. 10.1002/anie.198607311 Web of Science®Google Scholar 10B. Halton, M. J. Cooney, C. S. Jones, R. Boese, D. Bläser, Org. Lett. 2004, 6, 4017–4020. 10.1021/ol048307g CASPubMedWeb of Science®Google Scholar 11It is well recognized that annelation of the cyclopropene ring into an aromatic framework significantly enhances its thermodynamic stability. See for examples: Google Scholar 11aB. Halton, P. J. Stang, Synlett 1997, 145–158; 10.1055/s-1997-723 CASWeb of Science®Google Scholar 11bB. Halton, Chem. Rev. 2003, 103, 1327–1370; 10.1021/cr010009z CASPubMedWeb of Science®Google Scholar 11cG. M. Dixon, B. Halton, Eur. J. Org. Chem. 2004, 3707–3713. 10.1002/ejoc.200400353 CASWeb of Science®Google Scholar 12E. A. Carter, W. A. Goddard III, J. Phys. Chem. 1986, 90, 998–1001. 10.1021/j100278a006 CASWeb of Science®Google Scholar 13 13aV. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2006, 312, 722–724; 10.1126/science.1126675 CASPubMedWeb of Science®Google Scholar 13bV. Lavallo, Y. Ishida, B. Donnadieu, G. Bertrand, Angew. Chem. 2006, 118, 6804–6807; 10.1002/ange.200602701 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 6652–6655; 10.1002/anie.200602701 CASPubMedWeb of Science®Google Scholar 13cD. Holschumacher, C. G. Hrib, P. G. Jones, M. Tamm, Chem. Commun. 2007, 3661–3663; 10.1039/b706708a CASPubMedWeb of Science®Google Scholar 13dW. W. Schoeller, G. D. Frey, G. Bertrand, Chem. Eur. J. 2008, 14, 4711–4718. 10.1002/chem.200701926 CASPubMedWeb of Science®Google Scholar 14J. T. DePinto, W. A. deProphetis, J. L. Menke, R. J. McMahon, J. Am. Chem. Soc. 2007, 129, 2308–2315. 10.1021/ja066300j CASPubMedWeb of Science®Google Scholar 15 15aG. Trinquier, J. P. Malrieu, J. Am. Chem. Soc. 1987, 109, 5303–5315; 10.1021/ja00252a002 CASWeb of Science®Google Scholar 15bJ. P. Malrieu, G. Trinquier, J. Am. Chem. Soc. 1989, 111, 5916–5921; 10.1021/ja00197a061 CASWeb of Science®Google Scholar 15cH. Jacobsen, T. Ziegler, J. Am. Chem. Soc. 1994, 116, 3667–3679. 10.1021/ja00088a001 CASWeb of Science®Google Scholar 16 16aR. West, D. C. Zecher, S. W. Tobey, J. Am. Chem. Soc. 1970, 92, 168–172; 10.1021/ja00704a027 CASWeb of Science®Google Scholar 16bR. West, D. C. Zecher, W. Goyert, J. Am. Chem. Soc. 1970, 92, 149–154. 10.1021/ja00704a024 CASWeb of Science®Google Scholar 17 17aR. Breslow, P. Gal, J. Am. Chem. Soc. 1959, 81, 4747–4748; 10.1021/ja01526a077 CASWeb of Science®Google Scholar 17bR. Breslow, P. Gal, H. W. Chang, L. J. Altman, J. Am. Chem. Soc. 1965, 87, 5139–5144. 10.1021/ja00950a028 CASWeb of Science®Google Scholar 18 18aA. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, H. Schill, Top. Curr. Chem. 2000, 207, 89–147; 10.1007/3-540-48255-5_3 CASWeb of Science®Google Scholar 18bA. de Meijere, S. I. Kozhushkov, Chem. Rev. 2006, 106, 4926–4996. 10.1021/cr0505369 CASPubMedWeb of Science®Google Scholar 19CCDC 693680 (6 a) and 698793 (7 b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Google Scholar 20Z. Yoshida, Y. Tawara, Tetrahedron Lett. 1971, 12, 3603–3606. 10.1016/S0040-4039(01)97241-7 Google Scholar 21Cyclopropenones are notorious for inducing skin sensitivity and dermatitis. Google Scholar Citing Literature Volume121, Issue3January 5, 2009Pages 525-528 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Referência(s)