Rg. Coombes et al., THE MECHANISM OF NITRATION OF 2,4,6-TRIALKYLPHENOLS BY NITROGEN-DIOXIDE IN SOLUTION, Tetrahedron letters, 34(52), 1993, pp. 8557-8560
The apparent rate of reaction of 2,4,6-trialkylphenols with nitrogen d
ioxide in solution is that of a 6-nitrocyclohexa-2,4-dien-1-one to 4-n
itrocyclohexa-2,5-dien-1-one isomerisation unless the 2- and 6-alkyl g
roups are sufficiently bulky when the rare limiting stage may involve
reaction between the appropriate phenoxy radical and NO2.