Premium
Dediazoniation of Arenediazonium Ions. Part XXII. Reactions of 2, 6‐Dialkyl‐Substituted Benzenediazonium Ions in Super Acids, Acetonitrile and Acetone
Author(s) -
Laali Khosrow,
Szele Ivanka,
Zollinger Heinrich
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660612
Subject(s) - chemistry , acetonitrile , heterolysis , acetone , steric effects , diazonium compounds , medicinal chemistry , ion , azo coupling , polymer chemistry , organic chemistry , catalysis
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.