Selective Meta-Deprotonation of Toluene by Using Alkali-Metal-Mediated Magnesiation

Back to bases: Conventional organometallic bases usually deprotonate toluene at the methyl position to generate resonance‐stabilized benzyl anions, but using a new type of bimetallic metalation, sodium‐mediated magnesiation, the thermodynamic position for deprotonation can be switched to the aromati...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2005-05, Vol.44 (22), p.3459-3462
Main Authors: Andrikopoulos, Prokopis C., Armstrong, David R., Graham, David V., Hevia, Eva, Kennedy, Alan R., Mulvey, Robert E., O'Hara, Charles T., Talmard, Christine
Format: Article
Language:English
Subjects:
deprotonation
inverse crown compounds
magnesium
metalation
sodium
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Summary:Back to bases: Conventional organometallic bases usually deprotonate toluene at the methyl position to generate resonance‐stabilized benzyl anions, but using a new type of bimetallic metalation, sodium‐mediated magnesiation, the thermodynamic position for deprotonation can be switched to the aromatic ring (see picture).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500379