Mechanistische Aspekte der Diels-Alder-Reaktion: Ein kritischer Rückblick
1980; Wiley; Volume: 92; Issue: 10 Linguagem: Alemão
10.1002/ange.19800921004
ISSN1521-3757
AutoresJuergen Sauer, Reiner Sustmann,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoAngewandte ChemieVolume 92, Issue 10 p. 773-801 Aufsatz Mechanistische Aspekte der Diels-Alder-Reaktion: Ein kritischer Rückblick† Prof. Dr. Jürgen Sauer, Prof. Dr. Jürgen Sauer Institut für Organische Chemie der Universität Universitätsstraße 31, D-8400 RegensburgSearch for more papers by this authorProf. Dr. Reiner Sustmann, Prof. Dr. Reiner Sustmann Institut für Organische Chemie der Universität Universitätsstraße 31, D-8400 Regensburg Fachbereich Chemie der Universität Universitätsstraße 5, D-4300 EssenSearch for more papers by this author Prof. Dr. Jürgen Sauer, Prof. Dr. Jürgen Sauer Institut für Organische Chemie der Universität Universitätsstraße 31, D-8400 RegensburgSearch for more papers by this authorProf. Dr. Reiner Sustmann, Prof. Dr. Reiner Sustmann Institut für Organische Chemie der Universität Universitätsstraße 31, D-8400 Regensburg Fachbereich Chemie der Universität Universitätsstraße 5, D-4300 EssenSearch for more papers by this author First published: Oktober 1980 https://doi.org/10.1002/ange.19800921004Citations: 382 † Professor Rolf Huisgen zum 60. Geburtstag gewidmet 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 Abstract Die Frage nach dem zeitlichen Ablauf der Bindungsschließung stellt sich bei allen Typen von Cycloadditionsreaktionen. Durch stereochemische Untersuchungen und Studien zur Regiospezifität sowie intensive kinetische Untersuchungen unter Berücksichtigung von Substituenten- und Solvenseffekten sowie Temperatur- und Druckabhängigkeit der Reaktion lassen sich in vielen Fällen mechanistische Aussagen über die Diels-Alder-Reaktion gewinnen. Theoretische Interpretationsversuche, ab-initio- und semiempirische Berechnungen, Modellbetrachtungen, die Anwendung der Grenzorbital-(FMO-)Methode sowie thermochemische Messungen ermöglichen eine Beschreibung der Energiehyperfläche dieser [4 + 2]-Cycloadditionen. Es wird versucht, unter Einschluß aller experimentellen und theoretischen Kriterien eine Abgrenzung der mechanistischen Alternativen – Einstufenreaktion versus Zweistufenreaktion – zu erreichen. References 1 O. Diels, K. Alder, Justus Liebigs Ann. Chem. 460, 98 (1928). 10.1002/jlac.19284600106 CASWeb of Science®Google Scholar 2 Zur Definition von Cycloadditionen siehe R. Huisgen, Angew. Chem. 80, 329 (1968); 10.1002/ange.19680800902 Google Scholar Angew. Chem. Int. Ed. Engl. 7, 321 (1968). 10.1002/anie.196803211 CASWeb of Science®Google Scholar 3 Den Literaturzugang bis 1967 findet man bei J. Sauer, Angew. Chem. 78, 233 (1966); 10.1002/ange.19660780403 Google Scholar Angew. Chem. 76, 76 (1967); Google Scholar Angew. Chem. 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