Mechanisms of Diazo Coupling Reactions. Part XXXII. The Diazoamino Rearrangement in 20% Acetonitrile/Aqueous Buffers
| Autor: | John R. Penton, Heinrich Zollinger, Richard P. Kelly |
|---|---|
| Rok vydání: | 1982 |
| Předmět: |
chemistry.chemical_classification
Aqueous solution Chemistry Organic Chemistry Salt (chemistry) Biochemistry Diazoamino Compounds Catalysis Coupling reaction Ion Inorganic Chemistry chemistry.chemical_compound Drug Discovery Polymer chemistry Organic chemistry Amine gas treating Diazo Physical and Theoretical Chemistry Acetonitrile |
| Zdroj: | Helvetica Chimica Acta. 65:122-132 |
| ISSN: | 1522-2675 0018-019X |
| Popis: | The rearrangements of 4′-methoxy-N-methyl- and N-methyl-4′-nitro-diatzoaminobenzene have been studied in 20% acetonitrile/aqueous buffers. The reactions are specifically acid catalyzed and involve pre-equilibrium formation of amine and diazonium salt followed by rate-limiting attack of the diazonium ion at a C-atom (C-coupling) to give the corresponding aminoazo compounds. There is no evidence to suggest that, under the present conditions, mechanisms other than the established Friswell-Green mechanism occur. The traditional two-stage synthesis of aminoazo compounds via isolated diazoamino compounds can therefore be replaced by a one stage process for amines which undergo initial attack at a N-atom by diazonium ion (N-coupling). |
| Databáze: | OpenAIRE |
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