Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion

Hussein, Mohanad A.; Tran, Uyen P. N.; Huynh, Vien T.; Ho, Junming; Bhadbhade, Mohan; Mayr, Herbert und Nguyen, Thanh V. (2019): Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion. In: Angewandte Chemie-International Edition, Bd. 59, Nr. 4: S. 1455-1459

Abstract

Tropylium bromide undergoes noncatalyzed, regioselective additions to a large variety of Michael acceptors. In this way, acrylic esters are converted into beta-bromo-alpha-cycloheptatrienylpropionic esters. The reactions are interpreted as nucleophilic attack of bromide ions at the electron-deficient olefins and the approach of the tropylium ion to the incipient carbanion. Quantum chemical calculations were performed to elucidate the analogy to the amine- or phosphine-catalyzed Rauhut-Currier reactions. Subsequent synthetic transformations of the bromo-cycloheptatrienylated adducts are reported.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1433-7851
• Sprache: Englisch