Title: A Remarkable Effect of Silyl Substitution on Electrocyclization of Vinylallenes
Abstract: Angewandte Chemie International Edition in EnglishVolume 34, Issue 13-14 p. 1476-1477 Communication A Remarkable Effect of Silyl Substitution on Electrocyclization of Vinylallenes Prof. Masahiro Murakami, Corresponding Author Prof. Masahiro Murakami Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorHideki Amii, Hideki Amii Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorKenichiro Itami, Kenichiro Itami Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorProf. Yoshihiko Ito, Corresponding Author Prof. Yoshihiko Ito Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this author Prof. Masahiro Murakami, Corresponding Author Prof. Masahiro Murakami Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorHideki Amii, Hideki Amii Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorKenichiro Itami, Kenichiro Itami Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this authorProf. Yoshihiko Ito, Corresponding Author Prof. Yoshihiko Ito Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Kyoto 606-01 (Japan). Telefax: Int. code + (75) 753-5668Search for more papers by this author First published: July 31, 1995 https://doi.org/10.1002/anie.199514761Citations: 30AboutPDF 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 kinetics and thermodynamics of the electrocyclization of vinylallenes are favorably influenced when a silyl substituent is introduced into the open-chain compound. A series of vinylallenes containing a silyl group at the vinyl terminus (1) gave good yields of the corresponding cyclobutenes 2 when heated at reflux in xylene. A theoretical explanation for this observation remains elusive. References 1 A. R. Bassindale, P. G. Taylor in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley Interscience, Chichester, 1989, p. 893. 2 E. W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, London, 1989. 3(a) T. Durst, L. Breau in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 675; (b) S. Niwayama, K. N. Houk, Tetrahedron Lett. 1993, 34, 1251, and references therein. 4(a) H. Hopf, Angew. Chem. 1970, 82, 703; Angew. Chem. Int. Ed. Engl. 1970, 9, 732; (b) H. Hopf, F. T. Lenich, Chem. Ber. 1973, 106, 3461; (c) D. J. Pasto, S.-H. Yang, J. Org. Chem. 1989, 54, 3544; (d) F. Toda, P. Garratt, Chem. Rev. 1992, 92, 1685, and references therein. 5(a) E. Gil-Av, J. Herling, Tetrahedron Lett. 1967, 1; (b) H. Hopf, Nachr. Chem. Tech. 1975, 23, 235; (c) R. Schneider, H. Siegel, H. Hopf, Liebigs Ann. Chem. 1981, 1812; (d) D. J. Pasto, W. Kong, J. Org. Chem. 1989, 54, 4028. 6 M. Murakami, H. Amii, N. Takizawa, Y. Ito, Organometallics 1993, 12, 4223. 7 Another facile and unidirectional cyclization of vinylallene has recently been found in retinoids: J. G. Rey, J. Rodriguez, A. R. de Lera, Tetrahedron Lett. 1993, 34, 6293. 8 Vinylallenes unsubstituted at C4 afforded complex mixtures of intractable compounds. 9(a) C. G. Pitt, J. Organomet. Chem. 1973, 61, 49; (b) J. C. Giordan, J. Am. Chem. Soc. 1983, 105, 6544; (c) J. Yoshida, T. Murata, S. Isoe, Tetrahedron Lett. 1986, 27, 3373; (d) H. Bock, Angew. Chem. 1989, 101, 1659; Angew. Chem. Int. Ed. Engl. 1989, 28, 1627. Citing Literature Volume34, Issue13-14July 31, 1995Pages 1476-1477 ReferencesRelatedInformation
Publication Year: 1995
Publication Date: 1995-07-31
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 39
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