20778-61-4

Upstream product

• 67-56-1 methanol 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 1988-75-6 4-bromo-2,4,6-tri-tert-butyl-2,5-cyclohexadiene-1-one 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 5457-60-3 4-chloro-2,4,6-tri-tert-butylcyclohexa-2,5-dienone 

Downstream Products

• 20784-82-1 2,3,5-Tri-tert.-butyl-cyclohexen-⁽⁵⁾-dion-(1,4) 
• 34105-76-5 3,5-di-tert-butyl-1,2-benzoquinone 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 20784-84-3 1-Acetoxy-2-hydroxy-3,6-di-tert-butylbenzene 
• 4971-61-3 2,4,6-tri-tert-butyl-4-hydroxy-2,5-cyclohexadienone 

Relevant academic research and scientific papers

Solvolysis of 4-halogeno-4-alkyl-2,6-di-tert-butylcyclohexa-2,5-dienones induced by positive halogen donors as electrophiles

Positive halogen donors such as N-iodosuccinimide (NIS) induce solvolysis of dienones 1, as model 4-halogenocyclohexa-2,5-dienones, in different hydroxylic solvents (ROH), yielding the 4-RO-cyclohexa-2,5-dienones (2). The rate of the solvolysis with NIS is highly dependent on the structure of ROH. The problem of such dependency is overcome by running the reaction in ROH diluted with MeCN, a polar aprotic solvent, in place of pure ROH; the rate of the reaction in the ROH-MeCN solvent mixture is almost independent of the structure (or the polarity) of ROH, and the reaction is completed faster or markedly faster than in neat ROH. The results suggest that the solvolysis rate is controlled by the polarity of the solvent system, although the hydrogen-bond acceptability of MeCN for dilution also accelerates the reaction. A mechanism for the solvolysis is proposed, involving electrophilic attack of a positive halogen donor at the halogen atom of 1, generating the 4-oxocyclohexa-2,5-dienyl cation intermediates (8) via the rate-limiting polar transition states. CSIRO 2013.

An electrolytic system that uses solid-supported bases for in situ generation of a supporting electrolyte from acetic acid solvent

Re-usability is trumps: The electrolytic system presented here (see graphic) has been used for the anodic acetoxylation of various compounds to provide the corresponding acetoxylated products in good to excellent yields. The acetoxylated products and the solid-supported bases can easily be separated by filtration, and the separated solid-supported bases can be re-used many times. (Chemical Equation Presented)

Oxidation by Cobalt(III) Acetate. Part 13. Oxidation of Substituted Phenols with Cobalt(III) Acetate in Acetic Acid

The oxidation of 2,6-di- and 2,4,6-tri-substituted phenols with cobalt(III) acetate has been investigated in acetic acid under an inert atmosphere; the former gave the corresponding diphenoquinones in excellent yields, and the latter yielded side-chain or nuclear acetoxylated products in moderate to good yields.

Formation of Quinol Ethers using (Diacetoxyiodo)benzene

The use of (diacetoxyiodo)benzene for the oxidative coupling of a hindered phenol with aliphatic alcohols or other phenols has been investigated.

Bond Fixation in Annulenes. 14. Synthesis of and Bond Shifting Equilibrium between 1,4- and 1,6-Di-tert-butylcyclooctatetraenes

Photolysis of the Diels-Alder adduct of 3,6-di-tert-butyl-o-benzoquinone and cyclobutadiene at ice-bath temperatures afforded the bicyclooctatriene 12.During warming to room temperature, this hydrocarbon underwent kinetically first-order valence isomerization to provide 5 and its bond shift isomer 4.This finding adumbrated the facility with which 4 and 5 are interconverted.Reaction of this cyclooctatetraene mixture with N-methyltriazolinedione gave urazoles 16 and 17 as chromatographically separable entities.Like 13, the related cycloadduct of 12 wherein both bridgehead tert-butyl groups exhibit restricted rotation , the angular tert-butyl substituent in 17 is sterically perturbed.Hydrolysis-oxidation of either 16 or 17 returned only mixtures of 4 and 5 because of their rapid bond shifting rates.When the equilibrium constant between these two isomers was determined by 1H NMR spectroscopy, it was found that 5, the apparently more congested compound, was the more stable in CDCl3 solution.The possible underlying causes of this phenomenon are discussed.