Mild persubstitution of di- and tetrabrominated arenes with arylthiolate nucleophiles

A mild selective protocol was used to prepare tetrakis(2-chlorophenylthio)anthracene from tetrabromoanthracene and sodium 2-chlorobenzenethiolate avoiding the thiolate self-attack. The uncatalyzed nucleophilic substitution of a series of mono-, di-, and tetrabrominated arenes by arylthiolate ions wa...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (51), p.6730-6733
Main Authors: Del Rosso, Pablo G., Almassio, Marcela F., Bruno, Mattia, Garay, Raúl O.
Format: Article
Language:English
Subjects:
Aromatic compounds
Aromatic substitution
Atomic properties
Bromine
Nuclei
Nucleophiles
Organic materials
Persulfurated arenes
Purity
Selective sulfuration
Sodium
Tetrahedrons
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Summary:A mild selective protocol was used to prepare tetrakis(2-chlorophenylthio)anthracene from tetrabromoanthracene and sodium 2-chlorobenzenethiolate avoiding the thiolate self-attack. The uncatalyzed nucleophilic substitution of a series of mono-, di-, and tetrabrominated arenes by arylthiolate ions was attempted in mild conditions to investigate the scope of the substitution reaction regarding the size of the aromatic system as well as the number of bromine atoms. Successful reactions afforded only the persubstituted products in good purity and yield after a simple workup and chemoselectivity of Br versus Cl substituents was achieved for the tetrabromide.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.10.069