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Diels-Alder-Reaktion und deren 3D-Visualisierung

Literaturbeispiel [11] von Ignatovich et al.: Synthese, Kristall- und Molekülstruktur von 5-Trimethylgermyl-7-oxabicyclo[2.2.1]hept-5-en-2,3-exodicarbonsäureanhydrid

Derivatereaktion für die Diels-Alder-Reaktion von Furan und Maleinsäureanhydrid

Ignatovich et al. haben durch Kreuzkupplung im Ultraschallbad eine Germanium-organische Verbindung synthetisiert, die nachfolgend in einer Diels-Alder-Reaktion mit Maleinsäureanhydrid umgesetzt wird.

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Literaturreaktion [11] von Ignatovich et al.

Informationen zur Literaturreaktion [11]

Titel:
Synthese, Kristall- und Molekülstruktur von 5-Trimethylgermyl-7-oxabicyclo[2.2.1]hept-5-en-2,3-exodicarbonsäureanhydrid
Abstract:
Mittels Ultraschall-unterstützter Kreuzkupplungs-Reaktion wird aus 3-Brom-furan (I) und Trimethylgermaniumchlorid (II) das Furylgermanium (III) erhalten, das nach Diels-Alder-Reaktion die Titelverbindung (V) ergibt. Laut Röntgenstrukturanalyse liegt im Feststoff eine exo-Konformation vor (Raumgruppe P21/c, Z=4).
Literatur:
Ignatovich, L.; Priede, E.; Kemme, A.; Lukevics , E. (1992): Synthesis and Crystal and Molecular Structure of 5-Trimethylgermyl-7- oxabicyclo[2.2.1]hept-5-ene-2,3-exo-dicarboxylic Anhydride. In: J. Chem. Res., Synop.. 10 , 354

Literatur

Essers, M.; Wibbeling, B.; Haufe, G. (2001): Synthesis of the First Fluorinated Cantharidin Analogues. In: Tetrahedron Lett.. 42 (32) , 5429-5433ISSN: 0040-4039
Titel des Artikels
Synthesis of the First Fluorinated Cantharidin Analogues
Abstract
The synthesis of fluorinated cantharidines and related fluorinated endothall analogues is based on an exo-selective Diels-Alder reaction of fluorinated maleic anhydride with furan.
Dauben, W. G.; Lam, J. Y.; Guo, Z. R. (1996): Total Synthesis of (-)-Palasonin and (+)-Palasonin and Related Chemistry. In: J. Org. Chem.. 61 (14) , 4816-4819ISSN: 0022-3263
Titel des Artikels
Total Synthesis of (-)-Palasonin and (+)-Palasonin and Related Chemistry
Abstract
The biologically active (±)-palasonin, isolated formerly from Butea frondosa, is synthesized efficiently and resolved by standard methods into (+)- and (-)-palasonin. The Diels-Alder reaction between (I) and (II) is neither accelerated by a high reaction temperature nor by the use of the Grieco reagent (5 M LiClO4 in Et2O).
Song, Z. Z.; Ho, M. S.; Wong, H. N. (1994): Regiospecific Synthesis of 3,4-Disubstituted Furans. Part 7. Synthesis and Reactions of 3,4-Bis(trimethylsilyl)furan: Diels-Alder Cycloaddition, Friedel-Crafts Acylation, and Regiospecific Conversion to 3,4-Disubstituted Furans. In: J. Org. Chem.. 59 (14) , 3917-3926ISSN: 0022-3263
Titel des Artikels
Regiospecific Synthesis of 3,4-Disubstituted Furans. Part 7. Synthesis and Reactions of 3,4-Bis(trimethylsilyl)furan: Diels-Alder Cycloaddition, Friedel-Crafts Acylation, and Regiospecific Conversion to 3,4-Disubstituted Furans
Abstract
The title compound (III) is found to undergo Diels-Alder reaction with maleic anhydride to afford the adduct (V). However, with the acetylenes (VI) the products (VII) are obtained by a retro-Diels-Alder reaction. Friedel-Crafts acylation of (III) leads to α-substituted furans in general. In some cases protodesilylation also takes place. Different 3,4-disubstituted furans like (XVIII) are available via an efficient cross-coupling of boroxines generated from ipso displacement of Tms groups with BCl3 .
Tochtermann, W.; Bruhn, S.; Wolff, C. (1994): A Simple Access to 4,9-Epoxy-octahydroazulenelactones. In: Terahedron Lett.. 35 (8) , 1165-1168ISSN: 0040-4039
Titel des Artikels
A Simple Access to 4,9-Epoxy-octahydroazulenelactones
Abstract
Diels-Alder reaction of (I) and (II) gives a mixture of the exo and endo products; after isomerization the exo adduct (III) is obtained as the single product, which is further transformed to the title compounds (V) and (VI).
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