53379-63-8

Upstream product

• 74346-20-6 4-Brom-2,6-dimethylbenzoylchlorid 
• 506-82-1 dimethylcadmium 
• 83759-88-0 1-(4-amino-2,6 dimethylphenyl)ethanone 
• 114820-21-2 1-acetyl-2,6-dimethylbenzene-4-diazonium tetrafluoroborate 
• 74331-91-2 1-(2,6-Dimethyl-4-methoxyphenyl)vinyl chloride 
• 64-19-7 acetic acid 

Downstream Products

• 74346-32-0 1-(4-Bromo-2,6-dimethylphenyl)vinyl chloride 
• 1203605-38-2 5-(4-bromo-2,6-dimethyl-phenyl)-3-chloro-[1,2,4]triazine 
• 1203604-04-9 5-(4-Bromo-2,6-dimethylphenyl)-N-[(5-methoxy-1,3-benzothiazol-2-yl)methyl]-1,2,4-triazin-3-amine 
• 1203604-73-2 [5-(2,6-dimethyl-phenyl)-[1,2,4]triazin-3-yl]-(5-methoxy-benzothiazol-2-ylmethyl)-amine 
• 1203604-74-3 N-(4-{3-[(5-methoxy-benzothiazol-2-ylmethyl)-amino]-[1,2,4]triazin-5-yl}-3,5-dimethyl-phenyl)-acetamide 
• 1203604-76-5 (5-Methoxy-benzothiazol-2-ylmethyl)-{5-[4-(6-methoxy-pyridin-3-yl)-2,6-dimethyl-phenyl]-[1,2,4]triazin-3-yl}-amine 
• 118738-93-5 1-acetyl-2,6-dimethylbenzene-4-carbonitrile 

Relevant academic research and scientific papers

Protiodeacylation of 4-Substituted 1-Acetyl-2,6-dimethylbenzenes in Sulphuric Acid: Kinetics and Mechanism

In 89.8percent (w/w) sulphuric acid rate coefficients (1E4k1/s-1) for the protiodeacetylation of 4-substituted (X) 1-acetyl-2,6-dimethylbenzenes (1) were, at 25 deg C; X=Br, 0.468; I, 0.509; Cl, 0.635; H, 1.345; F, 2.52; Ph, 31.5; t-Bu, 38.6; and Me, 47.2.At 25 deg C the reaction of the ketone (1; X=OMe) was too fast, and at 80 deg C reactions of the ketones (1; X=CONH2 or CO2H) were too slow, for convenient measurement.The carboxy nitrile (X=CN) underwent hydratation to the amide (X=CONH2) rather than protiodeacetylation.The rate coefficients at 25 deg C of eight ketones (1) gave an accurate Hammett correlation, with ?+ constants, giving ρ = -4.64+/-0.05.The reaction of 1-acetyl-2,4,6-trimethylbenzene (1; X=Me) was studied of a range of acidity (73.6-99.9percent sulphuric acid), and a maximum was found near 86.0percent acid.Rates were also measured in D2SO4-D2O.The mechanism is discussed.

Vinyl Cation Intermediates in Solvolytic and Electrophilic Reactions. 1. Solvolysis of α-Arylvinyl Derivatives

The solvolysis of 16 α-arylvinyl tosylates, bromides, and chlorides has been investigated in various alcohol-water mixtures and in acetic acid at several temperatures.All substrates were substituted with either 2-methyl or 2,6-dimethyl groups to accelerate the rates of reaction.The major or exclusive product isolated in most cases was the acetophenone arising from hydrolysis of the expected enol ethers or acetates during workup.The kinetics were simple first order in the vast majority of cases, with excess base added to prevent side reactions.Leaving group effects, Winstein-Grunwald m values, Schleyer Q values, and effects of solvent nucleophilicity all point to a limiting SN1 ionization generating a vinyl cation intermediate, in which there is little rear-side nucleophilic assistance by solvent.Substituent effects led to ρ values in the range -3.9 to -5.3 vs. ?+.Activation parameters are typical for an SN1 process, and ΔS% is insensitive to the presence of zero, one, or two o-methyl groups, as are the effects of solvent polarity on the rates.The results should therefore be directly comparable with other solvolytic or electrophilic reactions generating formally similar vinyl cation intermediates.