3114-67-8Relevant articles and documents
Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation
Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji
supporting information, p. 1315 - 1319 (2019/03/07)
The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
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.