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, Vol. 59, No. 4: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English