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Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion
Author(s) -
Hussein Mohanad A.,
Tran Uyen P. N.,
Huynh Vien T.,
Ho Junming,
Bhadbhade Mohan,
Mayr Herbert,
Nguyen Thanh V.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910578
Subject(s) - chemistry , carbanion , nucleophile , bromide , regioselectivity , halide , adduct , nucleophilic addition , amine gas treating , photochemistry , phosphine , michael reaction , addition reaction , organic chemistry , medicinal chemistry , catalysis
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.