856632-67-2

Upstream product

• 1138-52-9 3,5-Di-tert-butylphenol 
• 102453-90-7 4,6-Di-tert-butyl-benzochinon-1,2-mono-p-toluolsulfonylhydrazon 
• 102453-90-7 4,6-di-tert-butyl-1,2-benzoquinone 2-(tosylhydrazone) 
• 3383-21-9 3,5-di-tert-butyl-o-benzoquinone 

Downstream Products

• 747-75-1 7,9-di-tert-butyl-1,1,4,4-tetramethyl-benzo[b][1,2]diazeto[1,2-d][1,4,5]oxadiazepine-2,5-dione 
• 78749-34-5 3,5-Di-tert-butyl-5-(3,5-di-tert-butyl-2-hydroxy-phenylazo)-5H-furan-2-one 
• 82959-56-6 1,6-Di-tert-butyl-4-methoxy-2,3-dioxa-bicyclo[3.2.1]oct-6-en-8-one 
• 53904-87-3 α,γ-di-tert-butyl-γ-crotonolactone 
• 25661-20-5 6,8-di-tert-butyl-1,1-diphenyl-benzo[e][1,2]diazeto[1,2-c][1,3,4]oxadiazin-2-one 
• 816441-27-7 3,5-di-(tert-butyl)-2-hydroxyazo-4-methoxybenzene 
• 106407-07-2 7,9-di-tert-butyl-1,1,4,4-tetraphenyl-benzo[b][1,2]diazeto[1,2-d][1,4,5]oxadiazepine-2,5-dione 

Relevant academic research and scientific papers

Synthesis of ortho-Azophenols by Formal Dehydrogenative Coupling of Phenols and Hydrazines or Hydrazides

Azophenols are important chromophores and reagents in organic synthesis, with applications as pigments and molecular switches. Here, we describe a catalytic aerobic process that couples phenols and hydrazines or hydrazides for their synthesis. The key aromatic C?N bond is formed by condensation between the hydrazine or hydrazide and an ortho-quinone, which triggers a redox-isomerization to install the azo-functionality. Notable features include rapid access to highly functionalized azophenols with a range of electronic configurations, including “push–pull” systems, conditions that employ simple, unactivated substrates, occurrence at room temperature using an earth-abundant and commercially available copper catalyst, and production of water as the only stoichiometric byproduct.

IR and UV matrix photochemistry and solvent effects: the isomerization of diazocyclohexadienones (ortho quinone diazides) - detection of molecules with the 1,2,3-benzoxadiazole structure. A UV/Vis and IR absorption and UV photoelectron spectroscopic investigation

6-Diazo-2,4-cyclohexadienone and derivatives with fluoro, chloro, methyl, tert-butyl and methoxy substituents have been investigated by UV/Vis absorption, IR absorption and UV photoelectron spectroscopy.Spectral results obtained in the gas phase, in an argon matrix at 10 K and in n-hexane solution at room temperature reveal an equilibrium with the respective 1,2,3-benzoxadiazole isomers, thus disproving current textbook opinions.The 1,2,3-benzoxadiazole structure is derived from the agreement of observed and calculated vertical ionization energies, characteristic IRand UV/Vis absorption bands as well as selective IR and UV photochemical transformations.The relative concentration of the respective 1,2,3-benzoxadiazole in equilibrium with the diazoketone isomer strongly depends on the substituents and on solvent effects.The diazoketone structure is stabilized by hydrogen bonding and polar interactions.The most stable 1,2,3-benzoxadiazole in this study, the 5,7-di-tert-butyl derivative, is at least 6.3 kJ mol-1 more stable than its diazocyclohexadienone valence isomer, whereas 2,3,4,5-tetrafluoro-6-diazo-2,4-cyclohexadienone and 3-methoxy-6-diazo-2,4-cyclohexadienone did not isomerize to a notable extent.Energetic considerations for the stabilization of 1,2,3-oxadiazoles are discussed and compared with experimental and theoretical findings.

THERMOLYSIS OF STERICALLY HINDERED BENZOQUINONE DIAZIDES IN ACETYL ACETONE

The thermolysis of 2,6-di-tert-butyl-1,4-benzoquinone 4-diazide and 4,6-di-tert-butyl-1,2-benzoquinone 2-diazide in acetylacetone leads to the formation of 3-(4-hydroxy-3,5-di-tert-butylphenyl)-4-hydroxy-3-penten-2-one and 3-(2-hydroxy-3,5-di-tert-butylph