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Un nouveau mécanisme réactionnel en série aromatique: Addition ‐ substitution
Author(s) -
Aubort J.D.
Publication year - 1968
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19680510830
Subject(s) - chemistry , bromine , substitution reaction , methanol , medicinal chemistry , aqueous medium , electrophile , aqueous solution , organic chemistry , catalysis
Reactions of three disubstituted sodium phenolsulfonates with bromine are examined in various conditions. In aqueous medium, two reactions may occur: bromodesulfonation (an electrophilic substitution) or/and formation of corresponding p ‐benzoquinones. In methanol, only bromodesulfonation is observed. Formation of p ‐benzoquinones is explained by a solvolytic displacement on the quinoloid product of bromine addition on phenolsulfonate. A reaction scheme is proposed, which explains the observed effects of substrate structure and reaction medium.