Dediazoniations of arenediazonium ions. Part 26 Influence of Substituents on the Formation of Benzoic Acids in Reactions of Aryl-Cation-Type Intermediates with CO
✍ Scribed by Michael D. Ravenscroft; Peter Skrabal; Bettina Weiss; Heinrich Zollinger
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- German
- Weight
- 362 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
The N2-molecule-aryl-cation pair formed as the first intermediate in dediazoniations of arenediazonium ions can be trapped with CO in H 2 0 with formation of the corresponding arenecarboxylic acids. This reaction is considered as a model for the reverse of dediazoniation, since CO is isoelectronic with N2. The evaluation of the yields of arenecarboxylic acids formed from substituted benzenediazonium ions using Tuff's dual substituent parameter treatment demonstrates that the field reaction constant pF and the resonance reaction constant pR are positive and negative, respectively, as expected for a reaction which corresponds electronically to the addition of N2 to aryl cations.