Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion |
| |
| Authors: | Mohanad A Hussein Dr Uyen P N Tran Dr Vien T Huynh Dr Junming Ho Dr Mohan Bhadbhade Prof?Dr Herbert Mayr Dr Thanh V Nguyen |
| |
| Institution: | 1. School of Chemistry, UNSW Sydney, Australia;2. School of Chemistry, University of Sydney, Australia;3. Mark Wainwright Analytical Centre, UNSW Sydney, Australia;4. Department Chemie, LMU München, Germany |
| |
| Abstract: | Tropylium bromide undergoes noncatalyzed, regioselective additions to a large variety of Michael acceptors. In this way, acrylic esters are converted into β-bromo-α-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. |
| |
| Keywords: | Halogene Michael-Akzeptoren Reaktionsmechanismen Synthesemethoden Tropylium |
|
|
