Artigo Revisado por pares

Ein hoch stereoselektiver optischer Schaltprozeß auf der Basis von Donor‐Acceptor‐substituierten dissymetrischen Alkenen

1995; Wiley; Volume: 107; Issue: 3 Linguagem: Alemão

10.1002/ange.19951070314

ISSN

1521-3757

Autores

Wolter F. Jager, Johannes C. de Jong, Ben de Lange, Nina P. M. Huck, Auke Meetsma, Ben L. Feringa,

Tópico(s)

Axial and Atropisomeric Chirality Synthesis

Resumo

Angewandte ChemieVolume 107, Issue 3 p. 346-349 Zuschrift Ein hoch stereoselektiver optischer Schaltprozeß auf der Basis von Donor-Acceptor-substituierten dissymetrischen Alkenen† Dr. Wolter F. Jager, Dr. Wolter F. Jager Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDr. Johannes C. de Jong, Dr. Johannes C. de Jong Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDr. Ben de Lange, Dr. Ben de Lange Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDrs. Nina P. M. Huck, Drs. Nina P. M. Huck Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDrs. Auke Meetsma, Drs. Auke Meetsma Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorProf. Dr. Ben L. Feringa, Corresponding Author Prof. Dr. Ben L. Feringa Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this author Dr. Wolter F. Jager, Dr. Wolter F. Jager Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDr. Johannes C. de Jong, Dr. Johannes C. de Jong Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDr. Ben de Lange, Dr. Ben de Lange Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDrs. Nina P. M. Huck, Drs. Nina P. M. Huck Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorDrs. Auke Meetsma, Drs. Auke Meetsma Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this authorProf. Dr. Ben L. Feringa, Corresponding Author Prof. Dr. Ben L. Feringa Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Department of Organic and Molecular Inorganic Chemistry, Groningen Centre for Catalysis and Synthesis, University of Groningen, Nyenborgh 4, NL-9747 AG Groningen (Niederlande), Telefax: Int. + 50/634296Search for more papers by this author First published: 7. Februar 1995 https://doi.org/10.1002/ange.19951070314Citations: 21 † Diese Arbeit wurde von der Technology Foundation (STW) und der Dutch Foundation for Scientific Research (NWO) gefördert und in Zusammenarbeit mit den Philips Research Laboratories (Niederlande) durchgeführt. AboutPDF 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 References 1(a) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; 10.1016/S0040-4020(01)81913-X CASWeb of Science®Google Scholar(b) M. Emmelius, G. Pawlowski, H. W. Vollmann, Angew. Chem. 1989, 101, 1475; 10.1002/ange.19891011104 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 1989, 28, 1445. 10.1002/anie.198914453 Web of Science®Google Scholar 2(a) Übersicht: H. Dürr, Angew. Chem. 1989, 101, 427; 10.1002/ange.19891010405 CASGoogle Scholar Angew. Chem. Int. Ed. 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Soc. 1991, 113, 5468. 10.1021/ja00014a057 CASWeb of Science®Google Scholar 6 Der Ausdruck „Pseudoenantiomere”︁ soll die entgegengesetzte Helicität von P-3 und M-4 vermitteln. Google Scholar 7(a) D. H. R. Barton, B. J. Willis, J. Chem. Soc. Perkin Trans. 1 1972, 305; Google Scholar(b) R. M. Kellogg, J. Buter, S. Wassenaar, J. Org. Chem. 1972, 37, 4045; 10.1021/jo00798a016 CASWeb of Science®Google Scholar(c) A. Schönberg, B. König, E. Singer, Chem. Ber. 1967, 100, 767. 10.1002/cber.19671000310 Web of Science®Google Scholar 8 Die Isomere 3 und 4 lassen sich im 1H-NMR-Spektrum leicht unterscheiden: Das Singulett der Methylgruppe bei δ = 3.07 der Verbindung 3 (Dimethylaminogruppe in der trans-Position) erscheint durch den abschirmenden Effekt der Napthalingruppe in der Verbindung 4 hochfeldverschoben bei δ = 2.30 (Dimethylaminogruppe in der cis-Position). Google Scholar 9 Weitere Einzelheiten zu den Kristallstrukturuntersuchungen können beim Direktor des Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ, unter Angabe des vollständigen Literaturzitates angefordert werden. Google Scholar 10 Y. Okamoto, K. Hatada, J. Liq. Chromatogr. 1986, 9, 369. 10.1080/01483918608076642 CASWeb of Science®Google Scholar 11(a) W. F. Jager, Chiroptical Molecular Switches: Application of Inherently Dissymmetric Alkenes, Dissertation, Groningen, 1994; Google Scholar(b) W. F. Jager, B. de Lange, A. M. Schoevaars, B. L. Feringa, Tetrahedron: Asymmetry 1993, 4, 1481. 10.1016/S0957-4166(00)80349-3 CASWeb of Science®Google Scholar 12 Für das unsubstituierte Analogon von 4 (X = S, R1 = R2 = R3 = H, Abb. 1) wurde eine Racemisierungsbarriere von 120.9 ± 0.5 kJmol−1 gefunden, während für das unsubstituierte Derivat von 1 (X = CH2, R1 = R2 = R3 = H, Abb. 1) eine Barriere von 110.7 ± 0.5 kJmol−1 ermittelt wurde (siehe Lit. [11a]). Google Scholar 13 B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron Lett. 1992, 33, 2887. 10.1016/S0040-4039(00)78887-3 CASWeb of Science®Google Scholar 14 In Ethanol und Chloroform wurde auch nach 30 min Bestrahlung bei 300 nm kein photostationärer Zustand erreicht. Daraus folgt, daß die Quantenausbeute für die Isomerisierungsprozesse in diesen Lösungsmitteln um den Faktor 100 niedriger zu sein scheint als in n-Hexan. Google Scholar 15 Die Isomerenzusammensetzung des photostationären Zustandes bei Bestrahlung mit einer Wellenlänge λ ist gegeben durch: [3]/[4] = ΣΠ4→4°3/→3ΣΠ4→3°4. Google Scholar 16 E. W. Meijer, B. L. Feringa, Mol. Cryst. Liq. Cryst. 1993, 235, 169. 10.1080/10587259308055190 CASGoogle Scholar Citing Literature Volume107, Issue37. Februar 1995Pages 346-349 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

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