
%0 Journal Article
%A Hartshorn, MP 
%A Judd, MC 
%A Vannoort, RW 
%A Wright, GJ 
%T The Nitration of 4-Methylphenol, 3,4-Dimethylphenol and 3,4,5-Trimethylphenol With Nitrogen Dioxide
%J Australian Journal of Chemistry
%D 1989/05/01
%V 42
%N 5
%P 689-697
%K 
%R https://doi.org/10.1071/CH9890689
%U https://www.publish.csiro.au/paper/CH9890689 
%X Reaction of 4-methylphenol (la) with excess nitrogen dioxide in either benzene or dichloromethane gives the 4-nitro dienone (2a) and the 2,6-dinitrophenol (5). Similar reactions of 3,4-dimethylphenol (Ib) yields the 4-nitro dienone (2b), the 2,6-dinitrophenol (8) and the 4-hydroxy 2,6-dinitro dienone (9), while reaction of 3,4,5-trimethylphenol (1c) gives the 4-nitro dienone (2c), the 2,4-dinitro dienone (11) and the 2,4,6-trinitro dienone (12a). The reaction pathways by which these products are formed are described and the results of reactions of postulated intermediates with nitrogen dioxide presented. 
