Premium
Sulfonyl Hydrazones of Cyclic Amides and Quaternary Azo Sulfones of Heterocycles as Reagents in Azo Chemistry
Author(s) -
Hünig S.
Publication year - 1968
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196803351
Subject(s) - sulfonyl , chemistry , reagent , nucleophile , phenols , oxidative coupling of methane , methylene , azo coupling , limiting , hydrazine (antidepressant) , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , mechanical engineering , alkyl , chromatography , engineering
Sulfonyl hydrazones of cyclic amides undergo oxidative coupling with phenols and reactive methylene components. The reaction proceeds via the azo sulfones, which may be used as such, and which, as ambident cations, enter into many reactions with nucleophiles and extend the scope of oxidative coupling. The reaction with phenols is a two‐step process, in which the limiting cases k 1 ≪ k 2 , k 1 ≈ k 2 , and k 1 ≫ k 2 can be realized by slight variation of the reactants.