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Halide Anion Activated Reactions of Michael Acceptors with Tropylium Ion

preprint
submitted on 16.08.2019 and posted on 19.08.2019 by 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 are reported.

Funding

Novel organic architectures and functional materials from tropylium ions

Australian Research Council

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Anion transporters as therapeutic agents

Australian Research Council

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History

Email Address of Submitting Author

t.v.nguyen@unsw.edu.au

Institution

University of New South Wales, Sydney

Country

Australia

ORCID For Submitting Author

000-0002-0757-9970

Declaration of Conflict of Interest

The authors declare no conflicts of interest

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