92375-27-4Relevant articles and documents
ipso Nitration. XXV. Nitration of di-tert-butylphenols, α-(3,5-di-tert-butylphenoxy)isobutyric acid, and 3,5-di-tert-butylphenoxyacetic acid: formation of nitrodienones and nitrodienes containing a secondary nitro group
Cross, Gordon G.,Fischer, Alfred,Henderson, George N.
, p. 2803 - 2812 (2007/10/02)
Nitration of 2,6-di-tert-butylphenol in acetic anhydride or chloroform gives 2,6-di-tert-butyl-4-nitrophenol and 2-tert-butyl-4,6-dinitrophenol.The intermediates 2,6-di-tert-butyl-4-nitrocyclohexa-2,5-dienone and 2,6-di-tert-butyl-4,6-dinitrocyclohexa-2,4-dienone, have been observed by 1H and 13C nmr.Nitration of 2,4-di-tert-butylphenol gives succesively 2,4-di-tert-butyl-6-nitrocyclohexa-2,4-dienone, 2,4-di-tert-butyl-6-nitrophenol, 2,4-di-tert-butyl-4,6-dinitrocyclohexa-2,5-dienone, and 2-tert-butyl-4,6-dinitrophenol.Nitration of 3,5-di-tert-butylphenol gives succesively 3,5-di-tert-butyl-6-nitrocyclohexa-2,4-dienone, 3,5-di-tert-butyl-2-nitrophenol, 3,5-di-tert-butyl-2,4-dinitrocyclohexa-2,5-dienone, and 3,5-di-tert-butyl-2,6-dinitrophenol. 3,5-Di-tert-butyl-4-nitrocyclohexa-2,5-dienone and 3,5-di-tert-butyl-2,6-dinitrocyclohexa-2,4-dienone are also formed as intermediates.Nitration of 3,5-di-tert-butylphenoxyacetic and isobutyric acids gives in each case the 2-nitro derivative.Further nitration of 3,5-di-tert-butyl-2-nitrophenoxyacetic and isobutyric acids gives a mixture of the adducts 7,9-di-tert-butyl-6,10-dinitro-1,4-dioxaspirodeca-6,8-dien-2-one and its 6,8-dinitro-6,9-diene isomer from the former and their 3,3-dimethyl derivatives from the latter.No dinitro acids are formed.
