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

Prokopis C. Andrikopoulos; David R. Armstrong; David V. Graham; Eva Hevia; Alan R. Kennedy; Robert E. Mulvey; Charles T. O'Hara; Christine Talmard

doi:10.1002/anie.200500379

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

Prokopis C. Andrikopoulos, David R. Armstrong, David V. Graham, Eva Hevia, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara, Christine Talmard

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

91 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3459-3462
Number of pages	3
Journal	Angewandte Chemie
Volume	44
Issue number	22
Early online date	21 Apr 2005
DOIs	https://doi.org/10.1002/anie.200500379
Publication status	Published - 30 May 2005

Keywords

deprotonation
inverse crown compounds
magnesium
metalation
sodium

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10.1002/anie.200500379

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title = "Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation",

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.",

keywords = "deprotonation, inverse crown compounds, magnesium, metalation, sodium",

author = "Andrikopoulos, {Prokopis C.} and Armstrong, {David R.} and Graham, {David V.} and Eva Hevia and Kennedy, {Alan R.} and Mulvey, {Robert E.} and O'Hara, {Charles T.} and Christine Talmard",

year = "2005",

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T1 - Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation

AU - Andrikopoulos, Prokopis C.

AU - Armstrong, David R.

AU - Graham, David V.

AU - Hevia, Eva

AU - Kennedy, Alan R.

AU - Mulvey, Robert E.

AU - O'Hara, Charles T.

AU - Talmard, Christine

PY - 2005/5/30

Y1 - 2005/5/30

N2 - 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.

AB - 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.

KW - deprotonation

KW - inverse crown compounds

KW - magnesium

KW - metalation

KW - sodium

UR - http://onlinelibrary.wiley.com/doi/10.1002/anie.200500379/abstract

U2 - 10.1002/anie.200500379

DO - 10.1002/anie.200500379

M3 - Article

SN - 0044-8249

VL - 44

SP - 3459

EP - 3462

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 22

ER -

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

Abstract

Keywords

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

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