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Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones : A Novel Access to Highly Substituted Tetrahydrothiophenes

Affiliation/Institute
Institut für Organische Chemie, Technische Universität Braunschweig
Augustin, André U.;
Affiliation/Institute
Institut für Organische Chemie, Technische Universität Braunschweig
Sensse, Maximilian;
GND
1132099900
Affiliation/Institute
Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig
Jones, Peter G.;
GND
1141094398
Affiliation/Institute
Institut für Organische Chemie, Technische Universität Braunschweig
Werz, Daniel B.

Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogs, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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