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Alkylation of Nitroaromatics with Trialkylborane
Author(s) -
Shifman Anna,
Palani Namasivayam,
Hoz Shmaryahu
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000303)39:5<944::aid-anie944>3.0.co;2-i
Subject(s) - yield (engineering) , chemistry , radical , alkylation , alkyl , potassium , substrate (aquarium) , radical nucleophilic aromatic substitution , medicinal chemistry , organic chemistry , catalysis , materials science , nucleophilic aromatic substitution , nucleophilic substitution , geology , oceanography , metallurgy
A novel, facile, aromatic substitution reaction of nitroaromatics is described. When p ‐dinitrobenzene ( 1 ) is treated with trialkylborane in the presence of potassium tert ‐butoxide, it furnishes p ‐alkylnitrobenzene ( 2 ) in high yield. A tentative mechanism is suggested involving alkyl radicals and radical anions of the nitroaromatic substrate.