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Mechanisms of Diazo Coupling Reactions. Part XXX. N-Diazo coupling of p-chloroaniline in acetonitrile: Rate-Limiting proton transfer

✍ Scribed by John R. Penton; Heinrich Zollinger

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
607 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The N‐diazo coupling of p‐chloroaniline with p‐chlorobenzenediazonium tetrafluoroborate in acetonitrile at 30° shows non‐linear base catalysis by water. The results are interpreted in terms of the S~E~2 mechanism with rate‐limiting proton loss at low base concentration; it is postulated, moreover that the reaction proceeds via transition states in which varying degrees of H‐bonding from the amine and the intermediate ω‐complex to different water species influence the initial step and the base catalysis.

📜 SIMILAR VOLUMES

Mechanisms of Diazo Coupling Reactions.
Mechanisms of Diazo Coupling Reactions. Part XXXI. Aminoazo formation in the diazo coupling of N, N-dimethylaniline and m-toluidine with p-methoxybenzenediazonium tetrafluoroborate in acetonitrile
✍ John R. Penton; Heinrich Zollinger 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 615 KB

## Abstract In the title reactions it is shown that aminoazo formation does not occur by direct attack of diazonium ion at C‐atom. Initial attack is at N‐atom, but proton loss from the ω~N~‐complex formed is relatively slow. Hence, at low amine concentration this rearranges intermolecularly to the

Mechanisms of Diazo Coupling Reactions.
Mechanisms of Diazo Coupling Reactions. Part XXXII. The Diazoamino Rearrangement in 20% Acetonitrile/Aqueous Buffers
✍ Richard P. Kelly; John R. Penton; Heinrich Zollinger 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 591 KB

## Abstract 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 at