ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 Nα-Nβ rearrangement (Eqn. 2), the exchange of the 15N-labelled diazo group with molecular nitrogen (Eqn. 3), and the reaction products was determined. With 0.3M 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), ArOCH2CF3 (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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640831
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