55649-30-4Relevant academic research and scientific papers
Phenoxazine: A privileged scaffold for radical-trapping antioxidants
Farmer, Luke A.,Haidasz, Evan A.,Griesser, Markus,Pratt, Derek A.
, p. 10523 - 10536 (2018/05/31)
Diphenylamines are widely used to protect petroleum-derived products from autoxidation. Their efficacy as radical-trapping antioxidants (RTAs) relies on a balance of fast H-atom transfer kinetics and stability to one-electron oxidation by peroxidic specie
Cyclodienones. Part 6. Preparation of 4-Azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone and its Thermal, Photo-, and Acid-catalyzed Decomposition
Fukata, Gouki,Sakamoto, Naoya,Tashiro, Massashi
, p. 2841 - 2848 (2007/10/02)
Preparation of 4-azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone (3) from 4-bromo-2,4,6-tri-t-butylcyclohexa-2,5-dienone (1) and sodium azide is described.Treatment of (3) with concentrated sulphuric acid afforded 2,6-di-t-butyl-p-benzoquinone (7) in 75percent yield, while the reaction at -10 deg C in chloroform solution gave a tri-t-butylazepinone (5) and 3,5-di-t-butyl-o-benzoquinone (8).Photolysis of (3) in benzene afforded 2,4-di-t-butylcyclopenta-2,4-dienone (11), which was isolated as the dimer (12).Thermolysis of (3) in boiling toluene gave 6-amino-2,4-di-t-butylphenol (17), 2,4,6,8-tetra-t-butyl-1H-phenoxazin-1-one (21), and 2-cyano-9,9a-dihydro-3,5,7,9a-tetra-t-butylcyclopentabenzoxazin-1(3aH)-one (22) in 15, 15 and 48percent yields, respectively.When the thermolysis was carried out with very low reagent concentrations, 5-cyano-2,4-di-t-butylcyclopenta-2,4-dienone (23), in addition to the phenol (17), was obtained.The compound (23) was also obtained by thermolysis of (3) in boiling acetic anhydride and in boiling toluene containing acetic anhydride.The reaction pathway for the formation of compounds (17), (22), and (23) on thermolysis of the azide (3) is also discussed.
