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Long-range Effect of Bromine in the Deprotonative Metalation of Aromatic Compounds

Authors :
Florence Mongin
Institut des Sciences Chimiques de Rennes (ISCR)
Université de Rennes 1 (UR1)
Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes)
Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes)
Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Source :
CHIMIA, Vol 70, Iss 1-2 (2016), CHIMIA, CHIMIA, Schweizerische Chemische Gesellschaft, 2016, The French Connection, 70 (1/2), pp.48-52. ⟨10.2533/chimia.2016.48⟩, CHIMIA, 2016, The French Connection, 70 (1/2), pp.48-52. ⟨10.2533/chimia.2016.48⟩
Publication Year :
2016
Publisher :
Swiss Chemical Society, 2016.

Abstract

Deprotonative metalation has been largely used to functionalize aromatic compounds. The efficiency of such reactions, as well as their regioselectivity, depends on the substituents connected to the rings. In contrast with other groups such as fluorine and methoxy, bromine exhibits a long-range acidifying effect. Here we try to depict this particular effect of bromine through different examples in which deprotometalation takes place at a remote position.

Details

Language :
German
ISSN :
26732424 and 00094293
Volume :
70
Issue :
1
Database :
OpenAIRE
Journal :
CHIMIA
Accession number :
edsair.doi.dedup.....d989247d112d441f3ac84d04446d663b
Full Text :
https://doi.org/10.2533/chimia.2016.48⟩