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Experimental Evidence for a Novel Limiting Mechanism of Aliphatic Nucleophilic Substitutions

1975; Wiley; Volume: 14; Issue: 1 Linguagem: Inglês

10.1002/anie.197500591

1521-3773

Tarek Elgomati, Dieter Lenoir, Ivar Ugi,

Photochemistry and Electron Transfer Studies

Angewandte Chemie International Edition in EnglishVolume 14, Issue 1 p. 59-61 Communication Experimental Evidence for a Novel Limiting Mechanism of Aliphatic Nucleophilic Substitutions† Tarek ElGomati, Tarek ElGomati Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this authorDr. Dieter Lenoir, Dr. Dieter Lenoir Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this authorProf. Dr. Ivar Ugi, Corresponding Author Prof. Dr. Ivar Ugi Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this author Tarek ElGomati, Tarek ElGomati Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this authorDr. Dieter Lenoir, Dr. Dieter Lenoir Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this authorProf. Dr. Ivar Ugi, Corresponding Author Prof. Dr. Ivar Ugi Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Institut für Organische Chemie der Technischen Universität, 8 München 2, Arcisstrasse 21 (Germany)Search for more papers by this author First published: January 1975 https://doi.org/10.1002/anie.197500591Citations: 17 † We thank Dr. Herbert Eck of Wacker-Chemie, Burghausen, for 3-ethoxycyclobutanone.—Support is acknowledged from the National Science Foundation, Grant G. P. 28927 X, the Deutsche Forschungsgemeinschaft, and the Fonds der Chemischen Industrie. 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 References 1 I. Lillien and L. Handloser, Tetrahedron Lett. 1970, 1243. 2 A. Streitwieser: Solvolytic Displacement Reactions. McGraw-Hill, New York, 1962, pp. 1–34, and literature cited therein. 3For the definition of ‘retention’ and ‘inversion’ see: (a) J. Gasteiger, P. Gillespie, D. Marquarding, and I. Ugi, Top. Curr. Chem. 48, 1 (1974); (b) J. Blair, J. Gasteiger, C. Gillespie, P. D. Gillespie, and I. Ugi, Tetrahedron 30, 1845 (1974). 4 L. Fowden, E. D. Hughes, and C. K. Ingold, J. Chem. Soc. 1955, 3187, and literature cited therein. 5See Ref. [2], pp. 11 and 12. 6 G. M. Lampman, G. D. Hager, and G. L. Couchan, J. Org. Chem. 35, 2398 (1970). 7 P. D. Gillespie and I. Ugi, Angew. Chem. 83, 493 (1971); Angew. Chem. internat. Edit. 10, 503 (1971), and literature cited therein. 8 I. Ugi, D. Marquarding, H. Klusacek, and P. Gillespie, Accounts Chem. Res. 4, 288 (1971); P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis, and I. Ugi, Angew. Chem. 83, 691 (1971); Angew. Chem. internat. Edit. 10, 687 (1971). 9(a) D. Marquarding, F. Ramirez, I. Ugi, and P. D. Gillespie, Angew. Chem. 85, 99 (1973); Angew. Chem. internat. Edit. 12, 91 (1973); (b) L. Tenud, S. Farooq, J. Seibl, and A. Eschenmoser, Helv. Chim. Acta 53, 2059 (1970). 10 H. Yamanaka, T. Yagi, K. Teramura, and T. Ando, Chem. Commun. 1971, 380; C. W. Jefford, U. Burger, M. H. Laffer, and T. Kabengele, Tetrahedron Lett. 1973, 2483. 11 J. T. Groves and K. W. Ma, Tetrahedron Lett. 1974, 909. 12(a) Pentacoordinate C-anions: A. M. Wooley and M. S. Child, Mol. Phys. 19, 625 (1970); A. Dedien and A. Veillard, J. Amer. Chem. Soc. 94, 6730 (1972); R. F. Bader, A. J. Duke, and R. R. Messer, J. Amer. Chem. Soc. 95, 7715 (1973); (b) Pentacoordinate cyclopropane derivatives: W. D. Stohrer, Chem. Ber. 107, 1795 (1974); CNDO/2 and ab initio calculations concerning the H⊖-adduct of 1,1-difluorocyclopropane were carried out at our institute by J. Gasteiger, W. Schubert, and R. Kopp. 13See Ref. [9a]: references [34], [49], [51–54], [57]; C. R. Hall and D. J. H. Smith, Tetrahedron Lett. 1974, 1696. 14 J. Emsley, T. B. Middleton, and J. K. Williams, J. C. S. Dalton 1974, 633. 15 L. H. Sommer: Stereochemistry, Mechanism and Silicon. McGraw-Hill, New York 1965; B. G. McKinnie, N. S. Bhacca, F. K. Cartledge, and J. Fayssonx, J. Amer. Chem. Soc. 96, 2537 (1974). Citing Literature Volume14, Issue1January 1975Pages 59-61 ReferencesRelatedInformation