15052-28-5Relevant articles and documents
Cyclohexadienone diazeniumdiolates from nitric oxide addition to phenolates
Scott Bohle,Imonigie, Jerome A.
, p. 5685 - 5692 (2000)
Sterically hindered phenols react with nitric oxide under basic condititons to give either cyclohexadienone diazeniumdiolates or oximates. Phenols with 2,6-di-tert-butyl and 4-methyl (butylated hydroxy toluene, BHT), 4-ethyl, or 4-methoxy methylene substituents yield the corresponding 2,6-di-tert-butyl-2,5-cyclohexadienone-4-alkyl-4-diazeniumdiolate salts (4-methyl 1a, 4-ethyl 3a, 4-methoxymethylene 5a). Phenols with 2,6-di-tert-butyl and 4-methylene (2,6-di-tertbutylphenol) substituents yield 4-methoxymethylenediazeniumdiolate (5a) together with 2,6-di-tert-butyl benzoquinone oximate (6a), while phenols with 2,6-di-tert-butyl and 4-methylenedimethylamino or hydrogen substituents yield exclusively 2,6-di-tert-butyl benzoquinone oximate (6a). Alkylation of the silver salts of 1a, or treating the O2-protonated diazeniumdiolate with diazomethane, both yield mixtures of O1- and O2-methylated isomers. All the compounds exhibit exothermic thermal decomposition except the quinuclidinium (1e, 3e, 5e) and triethylenediammonium (1f) salts which decompose endothermically. Three of the compounds namely 'O2-protonated' (Z)-1-[4-(2,6-di-tert-butyl-4-methyl-cyclohexadienonyl)]diazen-1-ium-1,2-diol inic acid (1b), O2-methyl (Z)-1-[4-(2,6-di-tert-butyl-4-methyl-cyclohexadienonyl)]diazen-1-ium-1,2-diol ate (1c), and 'O2-protonated' (Z)-1-[4-(2,6-di-tert-butyl-4-methoxymethylenecyclohexadienonyl)]diazen-1-ium -1,2-diolinic acid (5b) were characterized by single-crystal X-ray diffraction studies. The diazeniumdiolate framework in all the structures is coplanar with considerable π-bonding delocalized over the O-N-N-O framework.
Synthesis and crystal structure determination of 2,6-di-tert-butyl-4-(2,4, 6-triphenylpyridinium-1-yl)phenolate and its corresponding perchlorate salt
Shekhovtsov, Sergey V.,Omelchenko, Irina V.,Dyakonenko, Viktoriya V.,Shishkin, Oleg V.,Allmann, Rudolf,Libor, Thomas,Reichardt, Christian,McHedlov-Petrossyan, Nikolay O.
experimental part, p. 1394 - 1399 (2012/03/27)
2,6-Di-tert-butyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate belongs to the class of negatively solvatochromic dyes commonly used for the empirical determination of solvent polarities. By way of exception, it crystallizes without any solvent of crystallization due to the presence of two bulky tert-butyl groups in the phenolate moiety. The synthesis of this hydrophobic betaine dye has been improved and an X-ray crystal structure analysis of this solventless zwitterionic dye and its protonated form (as a perchlorate salt) has been carried out.
Photolysis of N-Alkoxybenzoquinone Imine N-Oxides
Baldry, Peter J.,Forrester, Alexander R.,Ogilvy, Munro M.,Thomson, Ronald H.
, p. 2035 - 2040 (2007/10/02)
Photolyses of a series of N-alkoxybenzoquinone imine N.oxides give products arising mainly from alkyl radicals, the solvent, and the several quinonoid species present in the reaction mixture.The alkyl radicals may be derived by fragmentation of the corresponding alkoxynitrenes which also rearrange to nitroso-compounds and hence to oximes.
