A Cycloaddition–Cyclodehydrogenation Route from Stilbenoids to Extended Aromatic Hydrocarbons
1995; Wiley; Volume: 34; Issue: 15 Linguagem: Inglês
10.1002/anie.199515831
ISSN1521-3773
AutoresMarkus Müller, Heike Mauermann‐Düll, Manfred Wagner, Volker Enkelmann, Kläus Müllen,
Tópico(s)Synthesis and characterization of novel inorganic/organometallic compounds
ResumoAngewandte Chemie International Edition in EnglishVolume 34, Issue 15 p. 1583-1586 Communication A Cycloaddition–Cyclodehydrogenation Route from Stilbenoids to Extended Aromatic Hydrocarbons† Dipl.-Chem. Markus Müller, Dipl.-Chem. Markus Müller Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDipl.-Chem. Heike Mauermann-Düll, Dipl.-Chem. Heike Mauermann-Düll Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDr. Manfred Wagner, Dr. Manfred Wagner Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDr. Volker Enkelmann, Dr. Volker Enkelmann Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorProf. Dr. Klaus Müllen, Corresponding Author Prof. Dr. Klaus Müllen Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this author Dipl.-Chem. Markus Müller, Dipl.-Chem. Markus Müller Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDipl.-Chem. Heike Mauermann-Düll, Dipl.-Chem. Heike Mauermann-Düll Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDr. Manfred Wagner, Dr. Manfred Wagner Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorDr. Volker Enkelmann, Dr. Volker Enkelmann Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this authorProf. Dr. Klaus Müllen, Corresponding Author Prof. Dr. Klaus Müllen Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350Search for more papers by this author First published: August 18, 1995 https://doi.org/10.1002/anie.199515831Citations: 70 † Dedicated to Professor Wolfram Grimme on the occasion of his 65th birthday AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 An unconventional route to planar graphitic fragments has been demonstrated with the novel synthesis of aromatic polycycles such as 2. The intramolecular Diels–Alder reaction of 1 is followed by aromatization and oxidative aryl–aryl coupling to afford 2 (C30H16) in high yield. The analogous synthesis of a C54H22 polyarene shows that this approach can be used to prepare larger graphitic sections. References 1 A. J. W. Tol, W. H. Laarhoven, J. Org. Chem. 1986, 51, 1663–1668; A. Böhm, K. Meerholz, J. Heinze, K. Müllen, J. Am. Chem. Soc. 1992, 114, 688–699. 2 A. Böhm, M. Adam, H. Mauermann, S. Stein, K. Müllen, Tetrahedron Lett. 1992, 33(20), 2795–2798. 3 R. Goddard, M. W. Haenel, W. C. Herndon, C. Krüger, M. Zander, J. Am. Chem. Soc. 1995, 117, 30–41. 4 C. Jubert, P. Knochel, J. Org. Chem. 1992, 57, 5425–5431; A. Sidduri, M. J. Rozema, P. Knochel, J. Org. Chem. 1993, 58, 2694–2713. 5 B. Fuchs, G. Scharf, J. Org. Chem. 1981, 46, 5395–5398. 6 Crystal structure analyses were conducted with a Nonius CAD-4 diffractometer with graphite-monochromated CuKα radiation (λ = 1.5418 Å) at room temperature. Lattice parameters were obtained from 25 reflections by least squares analysis (θ > 25°). The intensities were measured with θ/2θ scans. The structures were solved by direct methods, the C atoms refined with anisotropic deflection parameters, and the H atoms treated with a riding model. Empirical absorption correction; programs used: Molen, SIR, ORTEP. 3 (C30H24): monoclinic, C2/ c, a = 43.530(9), b = 5.632(3), c = 18.770(3) Å, β = 111.232(9)°, V = 4289.5 Å3, Z = 8, ρcalcd = 1.191 g cm−3, μ = 4.736 cm−1, 3011 reflections, of which 1799 were observed (I > 3σ(I)), R = 0.043, Rw = 0.047. 4c (C30H24): orthorhombic, P212121, a = 10.286(1), b = 11.433(1), c = 17.911(1) Å, V = 2106.2(5) Å3, Z = 4, ρcalcd = 1.213 g cm−3, μ = 4.823 cm−1, 1568 reflections, of which 1330 were observed (I > 3σ(I)), R = 0.033, Rw = 0.031. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany) on quoting the depository number CSD-58920. 7 In the HPLC separation a minor fraction (7 area %) was isolated, whose UV absorption maxima are red-shifted relative to those of the two diastereomeric pairs of enantiomers. This can be explained by a twofold 1,3-hydrogen shift converting the Diels–Alder product 4 into a phenanthrene. This phenanthrene derivative also yields diphenyltriphenylene 5 on dehydrogenation. 8 E. Clar, M. Zander, J. Chem. Soc. 1958, 1861–1865; H. Hopff, H. R. Schweizer, Helv. Chim. Acta 1959, 42, 2315–2333; A. H. A. Tinnemans, W. H. Laarhoven, J. Am. Chem. Soc. 1974, 96, 4617–4622; Y. Fujioka, Bull. Chem. Soc. Jpn. 1985, 58, 481–489. Citing Literature Volume34, Issue15August 18, 1995Pages 1583-1586 ReferencesRelatedInformation
Referência(s)