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submitted on 16.08.2019 and posted on 19.08.2019by Mohanad A. Hussein, Uyen P. N. Tran, Vien T. Huynh, Junming Ho, Mohan Bhadbhade, Herbert Mayr, Thanh Vinh Nguyen
Tropylium bromide undergoes non-catalyzed,
regioselective additions to a large variety of Michael acceptors. In this way,
acrylic esters are converted into ß-bromo-α-cycloheptatrienyl-propionic esters.
The reactions are interpreted by nucleophilic attack of bromide ions at the
electron-deficient olefins and trapping of the incipient carbanion by the
tropylium ion. 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