New synthesis of 1,2-diol monopropargyl ethers

Talybov, G. М.

doi:10.1134/s1070428017010225

Cited by 3 publications

(3 citation statements)

References 10 publications

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“…Antimicrobial properties have been determined by the zonal diffusion method. First, samples have been prepared for research, %: 0.25, 0.5 and 1.0 solutions of the synthesized compounds (7)(8)(9)(10)(11)(12) in the investigated oils and fuels. Next, 20-25 ml of nutrient medium has been poured into a Petri dish.…”

Section: General Techniques For the Preparation Of Oxiranes (7-12)mentioning

confidence: 99%

“…Among the most studied of such substituted oxiranes are glycidic esters obtained by the condensation of aromatic aldehydes with chloroacetic acid esters in the presence of bases (the Darzens reaction) [5]. In recent years, we have been studying various condensation reactions occurring in presence of chloromethyl propargyl ether [6][7][8]. In [6], we first carried out similar condensation of propargylchloromethyl ether with aromatic aldehydes (ketones) and obtained 2-aryl-1propargyloxiranes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of trans-2-benzyloxy-3(4-chloro(bromophenyl)oxiranes and their application as antimicrobial additives to oils and fuels

Talybov¹,

Akhmedova²,

Yusubov³

2022

SOCAR Proceedings

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The condensation reaction of chloromethylbenzyl ether with chloro(bromo)-substituted benzaldehydes in the presence of sodium hydroxide under the conditions of interphase catalysis (catalyst – TEBAC) has been studied. The synthesis method for 2-benzyloxy-3-aryloxiranes has been developed. The synthesis of oxiranes takes place stereoselectively with the formation of trans-isomers. The obtained compounds have been studied as antimicrobial additives for lubricating oils and fuels. Keywords: chloro(bromo)-substituted benzaldehydes; chloromethylbenzyl ether; trans-isomers; 2,3-disubstituted oxiranes; inretphase catalysis; antimicrobial additives.

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Section: General Techniques For the Preparation Of Oxiranes (7-12)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of trans-2-benzyloxy-3(4-chloro(bromophenyl)oxiranes and their application as antimicrobial additives to oils and fuels

Talybov¹,

Akhmedova²,

Yusubov³

2022

SOCAR Proceedings

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“…[1,2]. It is known that the interaction of chloromethylpropargyl ether with carbonyl compounds with the participation of metallic zinc leads to unsaturated oxyethers [3]. The interaction of chloromethylpropargyl(allyl) ether with phenacyl bromide, with the participation of the chiral catalyst -(+)benzotetramisole, can lead to the production of monoethers of α-glycols of allyl and propargyl alcohol of the aromatic series (1,2) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

SYNTHESIS AND DETERMINATION OF THE ABSOLUTE CONFIGURATION OF MONOETHERS OF Α-Glycols OF ALLYL AND PROPARGYL ALCOHOLS BY NMR 1H SPECTROSCOPY

2020

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The synthesis of previously unknown unsaturated aromatic oxyethers was carried out by reaction of chloromethylpropargyl(allyl) ether with phenacyl bromide, with the participation of the chiral catalyst - (+)-benzotetramisole, and their configurations were also established. It was shown the anisotropic effect of the phenyl group in the acid chloride of α-methoxytrifluoromethylphenylacetic acid (MTPA-Cl) on the halogenaryl group. Such effect leads to screening of the latter, and this, in turn, leads to a shift to a strong field and positive values of ∆δR/S, while proton signals of the less bulky group are shifted to a weaker field with a negative value of ∆δR/S. The interaction of chloromethylpropargyl (allyl) ether with phenacylbromide with the participation of the chiral catalyst - (+) - benzotetramisole leads to aromatic allyl and propargyl alcohol monoethers. By the chiral derivative agent (CDA) chloride anhydride- α-trifluoro-methyl-phenyl-acetic acid (MTPA-Cl) the absolute configuration of compounds was determined. Due to comparing the ΔδR/S data in the NMR 1H spectra during such interaction it was found that they converted to diastereomers.

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Determination of the Absolute Configuration of 1-[(4-(Bromomethyl)phenyl]-2-(prop-2-yn-1-yloxy)ethanol

Talybov

Baghirli

2020

Russ J Org Chem

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New synthesis of 1,2-diol monopropargyl ethers

Cited by 3 publications

References 10 publications

Synthesis of trans-2-benzyloxy-3(4-chloro(bromophenyl)oxiranes and their application as antimicrobial additives to oils and fuels

Synthesis of trans-2-benzyloxy-3(4-chloro(bromophenyl)oxiranes and their application as antimicrobial additives to oils and fuels

SYNTHESIS AND DETERMINATION OF THE ABSOLUTE CONFIGURATION OF MONOETHERS OF Α-Glycols OF ALLYL AND PROPARGYL ALCOHOLS BY NMR 1H SPECTROSCOPY

Determination of the Absolute Configuration of 1-[(4-(Bromomethyl)phenyl]-2-(prop-2-yn-1-yloxy)ethanol

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