The mechanism of nitration of 2,4,6-trialkylphenols by nitrogen dioxide in solution

Article abstract of DOI:10.1016/S0040-4039(00)61384-9

The apparent rate of reaction of 2,4,6-trialkylphenols with nitrogen dioxide in solution is that of a 6-nitrocyclohexa-2,4-dien-1-one to 4- nitrocyclohexa-2,5-dien-1-one isomerisation unless the 2- and 6-alkyl groups are sufficiently bulky when the rate limiting stage may involve reaction between the appropriate phenoxy radical and NO₂.