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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
Author(s) -
Penton John R.,
Zollinger Heinrich
Publication year - 1981
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.19810640603
Subject(s) - chemistry , diazo , amine gas treating , azo coupling , acetonitrile , ion , derivative (finance) , tetrafluoroborate , tertiary amine , dimethylaniline , coupling (piping) , photochemistry , atom (system on chip) , molecule , polymer chemistry , medicinal chemistry , organic chemistry , mechanical engineering , ionic liquid , computer science , financial economics , engineering , economics , embedded system , catalysis
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 aminoazo derivative. At high amine concentration a second method of aminoazo formation can take place involving attack of an amine molecule on the ω N ‐complex or on a molecular complex formed between the diazonium ion and the amine. Implication of these proposals for the diazoamino rearrangement are discussed.