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Sulfonyl Hydrazones of Cyclic Amides and Quaternary Azo Sulfones of Heterocycles as Reagents in Azo Chemistry

Identifieur interne : 001B78 ( Main/Exploration ); précédent : 001B77; suivant : 001B79

Sulfonyl Hydrazones of Cyclic Amides and Quaternary Azo Sulfones of Heterocycles as Reagents in Azo Chemistry

Auteurs : Hünig

Source :

RBID : ISTEX:FC1186DDC8E3F52284819023923BC4027E3366FF

Mots-clés :

Abstract

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 k1 ≪ k2, k1 ≈ k2, and k1 ≫ k2 can be realized by slight variation of the reactants.


Url:
DOI: 10.1002/anie.196803351


Affiliations:


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Le document en format XML

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<div type="abstract" xml:lang="en">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 k1 ≪ k2, k1 ≈ k2, and k1 ≫ k2 can be realized by slight variation of the reactants.</div>
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