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Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation

Andrikopoulos, Prokopis C. and Armstrong, David R. and Graham, David V. and Hevia, Eva and Kennedy, Alan R. and Mulvey, Robert E. and O'Hara, Charles T. and Talmard, Christine (2005) Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation. Angewandte Chemie, 44 (22). pp. 3459-3462. ISSN 0044-8249

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Abstract

Conventional meta-deprotonation of toluene leads to resonance of Benzylanionen. But with a new type of bimetallic metalation, the sodium-mediated Magnesierung, can shift the thermodynamic meta-deprotonation in the ring.