Nucleophilic Opening of the Oxirane Ring with Tetraalkylammonium Salt Anions in the Presence of Proton Donors

Bakhtin, Stanislav; Швед, Е. Н.; Синельникова, М. А.; Bespalko, Yulia

doi:10.1134/s1070428021040047

Cited by 4 publications

(2 citation statements)

References 27 publications

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“…From the analysis of literature materials [5,6] one can expect the above-mentioned reaction behavior proceed along the oxirane ring. The presence of this ring in the CHEMICAL PROBLEMS 2022 no.…”

Section: Resultsmentioning

confidence: 99%

“…For continuation of the research and with the aim of synthesizing unsaturated aromatic oxiranosilanes and oxiranosiloxanes [4][5] and revealing a comparative estimation of the chemical activity of two reactive centersthe acetylene bond and the oxirane ringand for clarification of the structural directionality, the addition reaction of trialkyl(aryl) hydridesilanes to 3-phenyl-1-methyl-1-glycidyloxyprop-2-ane in the presence of platinum-hydrochloric acid according to the scheme has been examined as follows:…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Askerov¹,

Mamedova²,

Nurullayeva³

et al. 2022

Chemical Problems

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The method of the synthesis of unsaturated aromatic oxiranosilanes by interaction of trialkyl- (aryl)-hydridesilanes with aromatic oxiranes of the acetylene series in the presence of catalyst (platinumhydrochloric acid) in a medium of absolute benzene (yield up to 82-85%) was developed and their properties studied. It was showed that the addition reaction proceeded on a triple bond according to Farmer's rule with the formation of trans-adducts and the maintenance of the oxirane ring. The composition and structure of the obtained unsaturated aromatic oxiranosilanes were confirmed by IR and PMR spectra. It revealed that the obtained unsaturated aromatic oxiranosilanes were highly reactive compounds and can undergo the reaction with nucleophilic and electrophilic reagents

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Askerov¹,

Mamedova²,

Nurullayeva³

et al. 2022

Chemical Problems

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Kinetic, Spectral and Mechanistic Regularities of New Reaction Systems With Chromogenic S_N2‐Type Reaction for Detection of Epoxy Compounds

Charyarov,

Bakhtin

2024

J of Physical Organic Chem

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New reaction systems “oxirane – nucleophile X– – proton‐donor reagent AH – solvent” have been proposed for the detection of epoxides in which nucleophilic opening of the oxirane ring occurs accompanied by the formation of a colored product. The kinetic and mechanistic regularities of reactions in the proposed systems were investigated. Reaction orders with respect to the components of the systems have been determined: close to 1 – for oxirane and X−, close to 0 – for AH. It was shown that the proposed chromogenic reactions represent nucleophilic substitution of SN2‐type and allow the detection of epoxides containing both a terminal and internal epoxy group, which can be used to monitor processes in systems where epoxides are either the initial compounds or the synthesis products. Based on the conducted studies, it is possible to develop methods for the quantitative determination of epoxides using kinetic methods of analysis and UV–visible spectroscopy.

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Organic Chemistry in Russian Universities. Achievements of Recent Years

Stoikov,

Antipin,

Burilov

et al. 2024

Russ J Org Chem

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Nucleophilic Opening of the Oxirane Ring with Tetraalkylammonium Salt Anions in the Presence of Proton Donors

Cited by 4 publications

References 27 publications

Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Kinetic, Spectral and Mechanistic Regularities of New Reaction Systems With Chromogenic S_N2‐Type Reaction for Detection of Epoxy Compounds

Organic Chemistry in Russian Universities. Achievements of Recent Years

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Nucleophilic Opening of the Oxirane Ring with Tetraalkylammonium Salt Anions in the Presence of Proton Donors

Cited by 4 publications

References 27 publications

Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Synthesis and Properties of Unsaturated Aromatic Oxiranosilanes

Kinetic, Spectral and Mechanistic Regularities of New Reaction Systems With Chromogenic SN2‐Type Reaction for Detection of Epoxy Compounds

Organic Chemistry in Russian Universities. Achievements of Recent Years

Contact Info

Product

Resources

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Kinetic, Spectral and Mechanistic Regularities of New Reaction Systems With Chromogenic S_N2‐Type Reaction for Detection of Epoxy Compounds