In:
Helvetica Chimica Acta, Wiley, Vol. 64, No. 8 ( 1981-12-16), p. 2721-2727
Abstract:
The dediazoniation of 2,4,6‐trimethylbenzenediazonium tetrafluoroborate ( 1 ) in 2,2,2‐trifluoroethanol (TFE) was studied in the presence of potassium thiocyanate. The effect of added salt on the dediazoniation rate, the N α ‐N β rearrangement ( Eqn. 2 ), the exchange of the 15 N‐labelled diazo group with molecular nitrogen ( Eqn. 3 ), and the reaction products was determined. With 0.3 M KSCN a dediazoniation‐rate increase of 16.5% was achieved, and the amounts of rearranged and exchanged product were reduced to 88% and 70%, respectively, of the values found in pure TFE. The dediazoniation products formed are ArF ( 3 ), ArOCH 2 CF 3 ( 4 ), ArSCN ( 5 ), ArNCS ( 6 ) and traces of 5, 7‐dimethylindazole ( 7 ). All the data are in agreement with, and support the previously proposed mechanism ( Equ. 1 ) of heterolytic dediazoniation of arenediazonium salts.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19810640831
Language:
English
Publisher:
Wiley
Publication Date:
1981
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
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