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Übergangsmetallaktivierte organische Verbindungen, XXXV. Ortho ‐Alkylierungen von aromatischen Azoverbindungen mit Alkyllithium‐Reagenzien und Lithiumtrimethylferrat(1‐)
Author(s) -
Kauffmann Thomas,
Jordan Jan,
Sander Jörg
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250125
Subject(s) - chemistry , methyllithium , medicinal chemistry , alkylation , reagent , stereochemistry , organic chemistry , catalysis
Transitional‐Metal‐Activated Organic Compounds, XXXV. — ortho ‐Alkylation of Aromatic Azo Compounds with Alkyllithium Reagents and Lithium Trimethylferrate(1‐) Whereas methyllithium reacts with 4‐(dimethylamino)‐, 4‐amino‐, and 4‐methoxyazobenzene, respectively, by ortho ‐methylation of the electron‐rich phenyl residue of the azo compound, (CH 3 ) 3 FeLi ortho ‐methylates the less electron‐rich phenyl group of 4‐(dimethylamino)azobenzene. A mechanistic rationalisation is given for both reaction modes.