Dediazoniation of Arenediazonium Ions. Part XXII. Reactions of 2, 6-Dialkyl-Substituted Benzenediazonium Ions in Super Acids, Acetonitrile and Acetone
✍ Scribed by Khosrow Laali; Ivanka Szele; Heinrich Zollinger
- Publisher
- John Wiley and Sons
- Year
- 1983
- Tongue
- German
- Weight
- 618 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Reactions of 2,4,6‐trimethylbenzenediazonium (1), 2,6‐diethylbenzenediazonium (2) and 2,6‐diisopropylbenzenediazonium (3) tetrafluoroborates were studied in magic acid, SbF~5~/SO~2~ClF, acetonitrile and acetone by ^1^H‐NMR and by analysis of the dediazoniation products. The N~α~‐N~β~ rearrangement of β‐N^15^‐labelled tetrafluoroborates 1–3 was followed by ^15^N‐NMR of the corresponding arylazonaphthols, as well as by MS analysis of the anilines obtained by reduction of the azo compounds. Diazonium salts 2 and 3 were synthesized for the first time and the steric effect of substituents at C(2) and C(6) on the reactions under study is discussed. All the results obtained can be rationalized by heterolytic dediazoniation of diazonium salts 1–3 and product formation from the corresponding aryl cations.