Halide Anion Activated Reactions of Michael Acceptors with Tropylium Ion

19 August 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

tropylium
bromide
Michael acceptor
olefin
addition

Supplementary materials

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TOC Nguyen
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Nguyen TropBr SI ChemRxiv
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Supplementary weblinks

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