Title: Cyclo[<i>d.e.d.e.e.d.e.d.e.e.</i>]decakisbenzene, a New Cycloarene
Abstract: Angewandte Chemie International Edition in EnglishVolume 25, Issue 8 p. 742-744 Communication Cyclo[d.e.d.e.e.d.e.d.e.e.]decakisbenzene, a New Cycloarene† Dipl.-Chem. Dirk J. H. Funhoff, Dipl.-Chem. Dirk J. H. Funhoff Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergSearch for more papers by this authorProf. Dr. Heinz A. Staab, Corresponding Author Prof. Dr. Heinz A. Staab Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergAbteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergSearch for more papers by this author Dipl.-Chem. Dirk J. H. Funhoff, Dipl.-Chem. Dirk J. H. Funhoff Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergSearch for more papers by this authorProf. Dr. Heinz A. Staab, Corresponding Author Prof. Dr. Heinz A. Staab Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergAbteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 HeidelbergSearch for more papers by this author First published: August 1986 https://doi.org/10.1002/anie.198607421Citations: 47 † Cycloarenes, a New Class of Aromatic Compounds, Part 5.—Part 4: [4]. 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 The new parent hydrocarbon 1 is the second cycloarene (after kekulene) that consists of twelve symmetrically arranged benzene rings. 1 forms yellow crystals and was prepared by photocyclization of a partially hydrogenated benzophenanthrenophanediene. Compound 1 contains 40 π electrons, but can be formulated with an inner and an outer [4n + 2] π-electron perimeter. References 1(a) H. A. Staab, F. Diederich, Chem. Ber. 116 (1983) 3487; (b) see also F. Diederich, H. A. Staab, Angew. Chem. 90 (1978) 383; Angew. Chem. Int. Ed. Engl. 17 (1978) 372. 2 H. A. Staab, F. Diederich, C. Krieger, D. Schweitzer, Chem. Ber. 116 (1983) 3504; see also C. Krieger, F. Diederich, D. Schweitzer, H. A. Staab, Angew. Chem. 91 (1979) 733; Angew. Chem. Int. Ed. Engl. 18 (1979) 699; D. Schweitzer, K. H. Hausser, H. Vogler, F. Diederich, H. A. Staab, Mol. Phys. 46 (1982) 1141. 3 H. A. Staab, F. Diederich, V. Čaplar, Liebigs Ann. Chem. 1983, 2262. 4 H. A. Staab, M. Sauer, Liebigs Ann. Chem. 1984, 742. 5 For the nomenclature of cycloarenes, see ref. [1a]. According to Chemical Abstracts rules, 2 is named 13,19: 14,18-dimethenoanthra[1,2-a]benzo[ o]pentaphene, which, however, reveals only poorly the structure and geometry of 2. There are no IUPAC rules that apply to this class of compounds. 6 Elemental analyses and spectroscopic data are in accord with the structure given. 7 17: 1H-NMR (360 MHz, CDCl3): δ = 1.36–1.46 (m, 4H; 7,8,22,23-Hax), 1.84–1.92 (m, 4H; 7,8,22,23-Heq), 2.29–2.35 (m, 2H; 7a,22a,-H), 2.61–2.77 (m, 8H; 6,9,21,24-H), 3.51 and 3.76 (AB, JAB = 13.5 Hz, 8H; 1,3,16,18-H), 3.86 (d, J = 5,0 Hz, 2H; 13b,28b-H), 6.67 (dd, J = 7.9 Hz and 2.0 Hz, 4H; 12,15,27,30-H), 6.89 (d, J = 2 Hz, 4H; 5,10,20,25-H), 6.97 (d, J = 7.9 Hz, 4H; 13,14,28,29-H).–13C-NMR (90.6 MHz, CDCl3): δ = 27.1, 27.9, 32.4, 36.0, 42.3, 126.4, 129.1, 130.4, 136.8, 137.2, 137.5.–MS (selected): m/z 584 (50%, M+), 292 (12), 291 (17), 261 (17), 259 (100). 8 A. Minsky, M. Rabinovitz, Synthesis 1983, 497. 9 G. Rohlfs, Diplomarbeit, Universität Heidelberg 1985. 10 3: 1H-NMR (360 MHz, C6D6): δ = 1.08–1.18 (m, 4H; 6,7,20,21-Hax), 1.52–1.56 (m, 4H; 6,7,20,21-Heq), 2.08–2.14 (m, 2H; 6a,20a-H), 2.21–2.28 (m, 4H; 5,8,19,22-Hax), 2.39–2.48 (m, 4H; 5,8,19,22-Heq), 3.65 (d, J = 5.0 Hz, 2H; 12b,26b-H), 6.74 (d, J = 7.8 Hz, 4H; 12,13,26,27-H), 6.77 (s, 4H; 1,2,15,16-H), 6.87 (d, J = 1.9 Hz, 4H; 4,9,18,23-H), 6.99 (dd, J = 7.8 and 1.9 Hz, 4H; 11,14,25,28-H). 11 C. Krieger, D. J. H. Funhoff, H. A. Staab, unpublished results. 12 D. Schweitzer, unpublished results. Citing Literature Volume25, Issue8August 1986Pages 742-744 ReferencesRelatedInformation
Publication Year: 1986
Publication Date: 1986-08-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 54
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