The ortho-alkylation of catechol

Belostotskaya, I. S.; Комиссарова, Н. Л.; Dzhuaryan, É. V.; Ершов, В. В.

doi:10.1007/bf00850511

Cited by 10 publications

(7 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…TBMHQ and TBHPC were prepared bases on the method as published by Belostotskaya (1972a) with some improvement. MHQ (5 g, 40 mmol) and 2.21 ml phosphoric acid (98%) as catalyst were added to a 500 ml three-neck flask.…”

Section: Materials and Chemicalsmentioning

confidence: 99%

See 1 more Smart Citation

Antioxidant activities of two novel synthetic methylbenzenediol derivatives

Huang¹,

Jiang²,

Liao³

et al. 2014

Czech J. Food Sci.

View full text Add to dashboard Cite

Huang Y., Jiang Z., Liao X., Hou J., Weng X. (2014): Antioxidant activities of two n o v e l synthetic methylbenzenediol derivatives. Czech J. Food Sci., 32: 348-353.2-(tert-Butyl)-5-methylbenzene-1,4-diol and 3-(tert-butyl)-5-methylbenzene-1,2-diol were synthesised by Friedel-Craft reaction of 2-methylbenzene-1,4-diol and 4-methylbenzene-1,2-diol, respectively, with tertiary butanol providing reasonable yields. The antioxidant activities of these two products, mother compounds and 2-(tert-butyl)benzene-1,4-diol were investigated and compared by means of 2,2-diphenyl-1-picrylhydrazyl radical and Rancim at test; 3-(tert-butyl)-5-methylbenzene-1,2-diol is the most potent antioxidant tested by using Rancimat test experiment. The 2,2-diphenyl-1-picrylhydrazyl radical scavenging abilities of 2-methylbenzene-1,4-diol, 4-methylbenzene-1,2-diol and 2-(tert-butyl) benzene-1,4-diol are almost equal and more than twice as strong as 2-(tert-butyl)-5-methylbenzene-1,4-diol and 3-(tert-butyl)-5-methylbenzene-1,2-diol. The antioxidant activities of the five compounds evaluated by Rancimat test mainly depend on their steric synergist effects between the two phenolic hydroxyl groups in their molecules. The antioxidant activities of the five compounds mainly depend on how many 2,2-diphenyl-1-picrylhydrazyl radicals can be scavenged by one mole of them in 2,2-diphenyl-1-picrylhydrazyl test. One mole of 2-methylbenzene-1,4-diol, 4-methylbenzene-1,2-diol and 2-(tert-butyl)benzene-1,4-diol can scavenge four moles of 2,2-diphenyl-1-picrylhydrazyl radicals, but one mole of 2-(tert-butyl)-5-methylbenzene-1,4-diol or 3-(tert-butyl)-5-methylbenzene-1,2-diol can only scavenge two mole 2,2-diphenyl-1-picrylhydrazyl radicals because 2,2-diphenyl-1-picrylhydrazyl radicals are very bulky.

show abstract

Section: Materials and Chemicalsmentioning

confidence: 99%

“…They could be synthesised in the traditional way (Morgenstern et al 1971;Belostotskaya et al 1972b) but in a low yield as the products were mixtures and had to be clarified. TBHPC has antioxidant activity (Diepgen et al 2011) and the ability of chelating with metal (Suzuki 1997).…”

mentioning

confidence: 99%

Antioxidant activities of two novel synthetic methylbenzenediol derivatives

Huang¹,

Jiang²,

Liao³

et al. 2014

Czech J. Food Sci.

View full text Add to dashboard Cite

show abstract

“…We synthesized 1,4- and 1,6-COT utilizing a modification of Paquette’s route starting with an ortho-alkylation of 1 using the method of Ershov et al (Scheme ). This was followed by a Corey–Suggs oxidation of 3,6-di- t- butyl-pyrocatechol ( 2 ) to 3,6-di- t- butyl- o -benzochinone ( 3 ). The Diels–Alder reaction of 3 with cyclobutadiene iron(II) tricarbonyl ( 4 ), synthesized via Pettit’s method, gave 1,6-di- t -butyltricyclo[4.2.2.0 0.25 ]deca-3,7-diene-9,10-dione ( 5 ) as a storable COT precursor from which the target compounds 1,4- and 1,6-COT can be prepared cleanly right before the NMR measurements via Strating–Zwanenburg photodecarbonylation .…”

mentioning

confidence: 99%

Intramolecular London Dispersion Interactions Do Not Cancel in Solution

et al. 2020

View full text Add to dashboard Cite

We present a comprehensive experimental study of a di-t-butyl-substituted cyclooctatetraene-based molecular balance to measure the effect of 16 different solvents on the equilibrium of folded versus unfolded isomers. In the folded 1,6-isomer, the two t-butyl groups are in close proximity (H•••H distance ≈ 2.5 Å), but they are far apart in the unfolded 1,4-isomer (H•••H distance ≈ 7 Å). We determined the relative strengths of these noncovalent intramolecular σ−σ interactions via temperature-dependent nuclear magnetic resonance measurements. The origins of the interactions were elucidated with energy decomposition analysis at the density functional and ab initio levels of theory, pinpointing the predominance of London dispersion interactions enthalpically favoring the folded state in any solvent measured. * sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c09597.Comparison with previous measurements as well as synthetic and computational details (PDF)

show abstract

“…Unless otherwise stated, all reagents were obtained from commercial sources and used without additional purification. 3,6-Di- tert -butyl- o -benzoquinone (Q 36 ) was prepared as described . Solvents were distilled over appropriate drying agents under argon prior to use.…”

Section: Methodsmentioning

confidence: 99%

Sterically Hindered Tellurium(IV) Catecholate as a Lewis Acid

et al. 2022

View full text Add to dashboard Cite

Sterically hindered tellurium catecholate Te(Cat36)2 (Cat36 = 3,6-di-tert-butyl-catecholate) was synthesized with the reaction of amorphous Te with 3,6-di-tert-butyl-o-benzoquinone. Adducts of Te(Cat36)2 with various O- and N-donors were isolated and characterized by means of single-crystal X-ray diffraction along with IR, UV–vis, and NMR (1H, 13C, and 125Te) spectroscopies. In the crystal structure of the adduct with 2,2′-bipyridine (bipy), the unprecedented μ-κ2 N,N′:κ2 N,N′-bridging coordination mode of bipy was observed. Various intermolecular interactions Te...O, Te...N, and Te...C in adducts were analyzed using density functional theory calculations and quantum theory of atoms in molecules analysis. The estimated strength for appropriate short contacts varies from 0.9 to 5.3 kcal/mol, and they are attractive and purely non-covalent.

show abstract

The ortho-alkylation of catechol

Cited by 10 publications

References 5 publications

Antioxidant activities of two novel synthetic methylbenzenediol derivatives

Antioxidant activities of two novel synthetic methylbenzenediol derivatives

Intramolecular London Dispersion Interactions Do Not Cancel in Solution

Sterically Hindered Tellurium(IV) Catecholate as a Lewis Acid

Contact Info

Product

Resources

About