One‐Step Synthesis of Benzotetra‐ and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene
2006; Wiley; Volume: 118; Issue: 39 Linguagem: Inglês
10.1002/ange.200602553
ISSN1521-3757
AutoresHirofumi Mukae, Hajime Maeda, Kazuhiko Mizuno,
Tópico(s)Fluorine in Organic Chemistry
ResumoAngewandte ChemieVolume 118, Issue 39 p. 6708-6710 Zuschrift One-Step Synthesis of Benzotetra- and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene† Hirofumi Mukae, Hirofumi Mukae Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this authorHajime Maeda Dr., Hajime Maeda Dr. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this authorKazuhiko Mizuno Dr., Kazuhiko Mizuno Dr. [email protected] Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this author Hirofumi Mukae, Hirofumi Mukae Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this authorHajime Maeda Dr., Hajime Maeda Dr. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this authorKazuhiko Mizuno Dr., Kazuhiko Mizuno Dr. [email protected] Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9289Search for more papers by this author First published: 29 September 2006 https://doi.org/10.1002/ange.200602553Citations: 7 † The authors thank Prof. H. Roth (The State University of New Jersey) for helpful discussions. The authors also thank Akihito Yamano and Motoo Shiro (Rigaku Corporation) for analysis of the X-ray crystallography data. This work was partially supported by Grants-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” (18037063 to K.M.), Exploratory Research (16655018 to K.M.), and Young Scientists (B) (16750039 to H.M.) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. 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 Die Bestrahlung von Acetonitrillösungen, die 1-Cyan-2-(4-pentenyl)naphthalinderivate enthalten, liefert über eine intramolekulare [2+3]-Photocycloaddition der Alkeneinheit an die 2,4-Positionen der Cyannaphthalineinheit in hohen Ausbeuten benzotetra- und benzopentacyclische Verbindungen mit Tri- und Tetrachinangerüsten (siehe Schema; n=1, 2). References 1J. Mattay, Tetrahedron 1985, 41, 2405–2417; 10.1016/S0040-4020(01)96636-0 CASWeb of Science®Google ScholarJ. Mattay, Tetrahedron 1985, 41, 2393–2404; 10.1016/S0040-4020(01)96635-9 CASWeb of Science®Google ScholarJ. J. McCullough, Chem. Rev. 1987, 87, 811–860; 10.1021/cr00080a008 CASWeb of Science®Google ScholarJ. Cornelisse, Chem. Rev. 1993, 93, 615–669; 10.1021/cr00018a002 CASWeb of Science®Google ScholarD. Döpp in Molecular and Supramolecular Photochemistry, Vol. 6 (Eds.: ), Marcel Dekker, New York, 2000, pp. 101–148; Google ScholarK. Mizuno, H. Maeda, A. Sugimoto, K. Chiyonobu in Molecular and Supramolecular Photochemistry, Vol. 8 (Eds.: ), Marcel Dekker, New York, 2001, pp. 127–241; Google ScholarN. Hoffmann in Molecular and Supramolecular Photochemistry, Vol. 12 (Eds.: ), Marcel Dekker, New York, 2005, pp. 529–552. Web of Science®Google Scholar 2P. A. Wender, J. J. Howbert, J. Am. Chem. Soc. 1981, 103, 688–690; 10.1021/ja00393a041 CASWeb of Science®Google ScholarP. A. Wender, R. Ternansky, M. deLong, S. Singh, A. Olivero, K. Rice, Pure Appl. Chem. 1990, 62, 1597–1602, and references therein. 10.1351/pac199062081597 CASWeb of Science®Google Scholar 3K. Mizuno, H. Maeda, Y. Inoue, A. Sugimoto, L. P. Vo, R. A. Caldwell, Tetrahedron Lett. 2000, 41, 4913–4916; 10.1016/S0040-4039(00)00718-8 CASWeb of Science®Google ScholarH. Maeda, S. Waseda, K. Mizuno, Chem. Lett. 2000, 1238–1239; 10.1246/cl.2000.1238 CASWeb of Science®Google ScholarH. Maeda, A. Sugimoto, K. Mizuno, Org. Lett. 2000, 2, 3305–3308; 10.1021/ol000193v CASPubMedWeb of Science®Google ScholarA. Yokoyama, K. Mizuno, Org. Lett. 2000, 2, 3457–3459. 10.1021/ol0002368 CASPubMedWeb of Science®Google Scholar 4J. J. McCullough, W. K. MacInnis, C. J. L. Lock, R. Faggiani, J. Am. Chem. Soc. 1980, 102, 7780–7782; 10.1021/ja00546a026 CASWeb of Science®Google ScholarJ. J. McCullough, W. K. MacInnis, C. J. L. Lock, R. Faggiani, J. Am. Chem. Soc. 1982, 104, 4644–4658. 10.1021/ja00381a023 CASWeb of Science®Google Scholar 5K. Mizuno, S. Konishi, T. Takata, H. Inoue, Tetrahedron Lett. 1996, 37, 7775–7778; 10.1016/0040-4039(96)01775-3 CASWeb of Science®Google ScholarK. Mizuno, S. Konishi, Y. Yoshimi, A. Sugimoto, Chem. Commun. 1998, 1659–1660; 10.1039/a803711f CASWeb of Science®Google ScholarY. Yoshimi, S. Konishi, H. Maeda, K. Mizuno, Tetrahedron Lett. 2001, 42, 3475–3477; 10.1016/S0040-4039(01)00468-3 CASWeb of Science®Google ScholarY. Yoshimi, S. Konishi, H. Maeda, K. Mizuno, Synthesis 2001, 1197–1202; 10.1055/s-2001-15068 CASWeb of Science®Google ScholarH. Maeda, H. Mukae, K. Mizuno, Chem. Lett. 2005, 34, 66–67. 10.1246/cl.2005.66 CASWeb of Science®Google Scholar 6D. Bryce-Smith, A. Gilbert, B. H. Orger, J. Chem. Soc. Chem. Commun. 1966, 512–514; CASGoogle ScholarY. Inoue, K. Nishida, K. Ishibe, T. Hakushi, N. J. Turro, Chem. Lett. 1982, 471–474; 10.1246/cl.1982.471 CASWeb of Science®Google ScholarN. Zupančič, B. Šket, J. Chem. Soc. Perkin Trans. 1 1992, 179–180. Web of Science®Google Scholar 7Related benzotricyclic compounds were obtained by di-π-methane rearrangement of [4+2] cycloadducts: D. Döpp, H. R. Memarian, Chem. Ber. 1990, 123, 315–319. 10.1002/cber.19901230216 Web of Science®Google Scholar 8For other examples of [3+2] photocycloaddition, see: I. Saito, K. Shimozono, T. Matsuura, Tetrahedron Lett. 1982, 23, 5439–5442; 10.1016/S0040-4039(00)85862-1 CASWeb of Science®Google ScholarT. Miyashi, Y. Takahashi, T. Mukai, H. D. Roth, M. L. M. Schilling, J. Am. Chem. Soc. 1985, 107, 1079–1080; 10.1021/ja00290a065 CASWeb of Science®Google ScholarP. H. Mazzocchi, C. Somich, M. Edwards, T. Morgan, H. L. Ammon, J. Am. Chem. Soc. 1986, 108, 6828–6829; 10.1021/ja00281a074 CASWeb of Science®Google ScholarH. Tomioka, D. Kobayashi, A. Hashimoto, S. Murata, Tetrahedron Lett. 1989, 30, 4685–4688; 10.1016/S0040-4039(01)80774-7 CASWeb of Science®Google ScholarK. Mizuno, K. Nire, H. Sugita, Y. Otsuji, Tetrahedron Lett. 1993, 34, 6563–6566; 10.1016/0040-4039(93)88105-R CASWeb of Science®Google ScholarH. Suginome, K. Kobayashi, A. Konishi, H. Minakawa, H. Sakurai, J. Chem. Soc. Chem. Commun. 1993, 807–809; 10.1039/c39930000807 CASWeb of Science®Google ScholarF. Müller, J. Mattay, S. Steenken, J. Org. Chem. 1993, 58, 4462–4464; 10.1021/jo00068a048 CASWeb of Science®Google ScholarY. Kubo, K. Kiuchi, I. Inamura, Bull. Chem. Soc. Jpn. 1999, 72, 1101–1108; 10.1246/bcsj.72.1101 CASWeb of Science®Google ScholarK. Mizuno, N. Ichinose, Y. Yoshimi, J. Photochem. Photobiol. C 2000, 1, 167–193; 10.1016/S1389-5567(00)00011-3 CASGoogle ScholarK. Mizuno, H. Sugita, T. Hirai, H. Maeda, Y. Otsuji, M. Yasuda, M. Hashiguchi, K. Shima, Tetrahedron Lett. 2001, 42, 3363–3366; 10.1016/S0040-4039(01)00462-2 CASWeb of Science®Google ScholarH. Maeda, Y. Miyata, K. Mizuno, Tetrahedron Lett. 2002, 43, 1481–1486. 10.1016/S0040-4039(02)00039-4 CASWeb of Science®Google Scholar 9A colorless block crystal of C20H15N3 with approximate dimensions of 0.70×0.50×0.30 mm3 was mounted on a glass fiber. All measurements were made on a Rigaku Raxis Rapid imaging plate area detector with graphite monochromated MoKα radiation. The data were collected at a temperature of 23±1 °C to a maximum 2θ value of 55.0°. Cell constants and an orientation matrix for data collection corresponded to a primitive triclinic cell with dimensions: a=6.803(4), b=10.585(6), c=11.665(9) Å; α=67.57(3), β=74.27(3), γ=85.95(2)°; V=746.8(8) Å3. The space group was determined to be P (no. 2). ρcalcd=1.322 g cm−3. The structure was solved by direct methods (SIR88) and expanded by using Fourier techniques. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined by using the riding model. The final cycle of full-matrix least-squares refinement on F was based on 2590 observed reflections (I>5.00σ(I)) and 224 variable parameters and was converged with unweighted and weighted agreement factors of R=0.0383 and Rw=0.0421. Google Scholar 10F. Hirayama, J. Chem. Phys. 1965, 42, 3163–3171. 10.1063/1.1696395 CASWeb of Science®Google Scholar 11Intramolecular photocycloaddition of 1-cyano-2-(4-pentenyl)benzene also proceeds by the 2,4-addition, 1,3-closure mode: H. A. Neijenesch, R. J. P. J. de Ruiter, E. J. Ridderikhoff, J. O. van den Ende, L. J. Laarhoven, L. J. W. van Putten, J. Cornelisse, J. Photochem. Photobiol. A 1991, 60, 325–343. 10.1016/1010-6030(91)90035-R CASWeb of Science®Google Scholar 12The addition of methanol in the photoreaction of 1 b did not afford any methanol-incorporated products via the dipolar intermediate. Google Scholar Citing Literature Volume118, Issue39October 6, 2006Pages 6708-6710 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)