
%0 Journal Article
%A Gray, MJ 
%A Hartshorn, MP 
%A Penfold, BR 
%A Vaughan, J 
%T The nitration of some substituted 4-methylphenols; X-ray crystal structure of (Z)-3-Bromo-5-(bromonitromethylene)furan-2(5H)-one
%J Australian Journal of Chemistry
%D 1984/01/01
%V 37
%N 1
%P 55-63
%K 
%R https://doi.org/10.1071/CH9840055
%U https://www.publish.csiro.au/paper/CH9840055 
%X The nitrations of 2-substituted 4-methyl-6-nitrophenols (1a),(l1b) and (1c) give 6-substituted 3-methyl-2-nitro-1,4-benzoquinones (2a), (2b) and (2c). Similar reaction of 2,3-dibromo-4-methyl- 6-nitrophenol (5) gives 2,3-dibromo-5-methyl-6-nitro-1,4-benzoquinone (7) and the 4-nitratocyclo- hexa-2,5-dienone (12). In contrast, 2,3,6-tribromo-(4a) and 2,6-dibromo-(4b) 4-methylphenols give 1,4-benzoquinones with loss of the methyl group. Lactone (18) was formed in the nitration of the 2,6-dibromophenol (4b) and its structure was determined by single-crystal X-ray analysis. 
