Abstract: Angewandte Chemie International EditionVolume 43, Issue 22 p. 2951-2955 Communication Doubly N-Confused Pentaphyrins Alagar Srinivasan Dr., Alagar Srinivasan Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorTomoya Ishizuka Dr., Tomoya Ishizuka Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorHiromitsu Maeda Dr., Hiromitsu Maeda Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorHiroyuki Furuta Prof. Dr., Hiroyuki Furuta Prof. Dr. [email protected] Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606 PRESTO, JSTSearch for more papers by this author Alagar Srinivasan Dr., Alagar Srinivasan Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorTomoya Ishizuka Dr., Tomoya Ishizuka Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorHiromitsu Maeda Dr., Hiromitsu Maeda Dr. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606Search for more papers by this authorHiroyuki Furuta Prof. Dr., Hiroyuki Furuta Prof. Dr. [email protected] Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-651-5606 PRESTO, JSTSearch for more papers by this author First published: 19 May 2004 https://doi.org/10.1002/anie.200453732Citations: 42 Read the full textAboutPDF 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 Adding to the confusion: [3+2] coupling of confused tripyrrane and confused dipyrromethane dicarbinol, followed by oxidation, results in the synthesis of meso-pentafluorophenyl-substituted, doubly N-confused, oxo-substituted pentaphyrins (see X-ray crystal structure; green: F, blue: N, red: O). The oxopyrrole moieties have been shown to readily form intra- and intermolecular hydrogen bonds. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53732_s.pdf or from the author. 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 1 1a The Porphyrin Handbook, Vol. 2 (Eds.: ), Academic, San Diego, 2000; 1bA. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267–2340; 1cJ. L. Sessler, S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Pergamon, New York, 1997. 2 2aH. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 767–768; 2bP. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. 1994, 106, 805–808; Angew. Chem. Int. Ed. Engl. 1994, 33, 779–781; 2cH. Furuta, H. Maeda, A. Osuka, Chem. Commun. 2002, 1795–1804; 2dL. Latos-Grażyński in ref. [1], chap. 14. 3 3aH. Furuta, H. Maeda, A. Osuka, J. Am. Chem. Soc. 2000, 122, 803–807; 3bH. Furuta, H. Maeda, A. Osuka, J. Org. Chem. 2000, 65, 4222–4226 (corrigendum: H. Furuta, H. Maeda, A. Osuka, J. Org. Chem. 2000, 65, 5450); 3cH. Furuta, H. Maeda, A. Osuka, J. Org. Chem. 2001, 66, 8563–8572; 3dK. Araki, H. Winnischofer, H. E. Toma, H. Maeda, A. Osuka, H. Furuta, Inorg. Chem. 2001, 40, 2020–2025; 3eH. Furuta, H. Maeda, A. Osuka, M. Yasutake, T. Shinmyozu, Y. Ishikawa, Chem. Commun. 2000, 1143–1144; 3fH. Maeda, A. 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Lett. 2003, 5, 1293–1296. 7 7aCrystal data for 4: C55H12N5OF25⋅2.5 H2O, Mr=1278.73, triclinic, space group P (no. 2), a=12.49(1), b=15.31(1), c=16.04(1) Å, α=119.09(7), β=97.56(7), γ=94.61(8)°, V=2619(3) Å3, Z=2, R=0.085, wR=0.1140, GOF=1.174; 7bcrystal data for 5: C55H12N5O2F25⋅C8H18, Mr=1363.92, triclinic, space group P (no. 2), a=12.2382(8), b=15.4371(10), c=16.2425(11) Å, α=97.9870(10), β=106.6900(10), γ=107.6360(10)°, V=2714.0(3) Å3, Z=2, R=0.064, wR=0.058, GOF=1.025; 7ccrystal data for 6: C57H11N5O4F25Rh⋅1.5 C6H14, Mr=1536.88, triclinic, space group P (no. 2), a=12.08(1), b=15.14(1), c=18.00(2) Å, α=98.80(8), β=100.48(8), γ=95.13(8)°, V=3212(5) Å3, Z=2, R=0.062, wR=0.086, GOF=1.030. CCDC-228400–228402 (4–6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or [email protected]). 8S. J. Silvers, A. Tulinsky, J. Am. Chem. Soc. 1967, 89, 3331–3337. 9A. Srinivasan, H. Furuta, A. Osuka, Chem. Commun. 2001, 1666–1667. 10M. Gouterman in The Porphyrins, Vol. 3 (Ed.: ), Academic, New York, 1978, pp. 1–165. 11 11aO. S. Mills, E. F. Paulus, J. Organomet. Chem. 1967, 10, 331–336; 11bO. S. Mills, J. P. Nice, J. Organomet. Chem. 1967, 10, 337–342. 12 12aH. Raxhausen, A. Gossauer, J. Chem. Soc. Chem. Commun. 1983, 275; 12bC. Brückner, E. D. Sternberg, R. W. Boyle, D. Dolphin, Chem. Commun. 1997, 1689–1690. 13J.-Y. Shin, H. Furuta, A. Osuka, Angew. Chem. 2001, 113, 639–641; Angew. Chem. Int. Ed. 2001, 40, 619–621. Citing Literature Volume43, Issue22May 24, 2004Pages 2951-2955 ReferencesRelatedInformation
Publication Year: 2004
Publication Date: 2004-05-19
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 43
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