
Helvetica Chimica Acta p. 1737 - 1747 (1983)
Update date:2022-08-05
Topics:
Laali, Khosrow
Szele, Ivanka
Zollinger, Heinrich
Reactions of 2,4,6-trimethylbenzenediazonium (1), 2,6-diethylbenzenediazonium (2) and 2,6-diisopropylbenzenediazonium (3) tetrafluoroborates were studied in magic acid, SbF5/SO2ClF, acetonitrile and acetone by 1H-NMR and by analysis of the dediazoniation products.The Nα-Nβ rearrangement of β-N15-labelled tetrafluoroborates 1-3 was followed by 15N-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 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.
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