Catalytic Isomerization of Substituted Vinylcyclopropanes

Раскильдина, Г. З.; Borisova, Yu. G.; Davletshin, A. R.; Злотский, С. С.

doi:10.1134/s0012500819070115

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…A whole range of cyclic and acyclic products can be formed from 2-norcarene (bicyclo[4.1.0]hept-2-ene) in pentane under irradiation (sources with wavelengths of 185–228 nm) including allene (heptatriene-1,2,6, 13% yield). 23 Several additional examples of the transformation of VCPs into CPs 24–34 are present in the literature, leading to various substituted molecules with a cyclopentene moiety (although not all the described reactions can be carried out under standard conditions, or at least with slight heating). 24,25 Importantly, most VCPs rearrangements show low regioselectivity.…”

Section: Introductionmentioning

confidence: 99%

Switchable light vs. acid-induced transformations of complex framework compounds at room temperature

et al. 2022

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Reversible rearrangements have been studied. UV induced conversion of 1-phenyl-3a-R2-3,3а,8,8а-tetrahydro-3,8-(epiminomethano)cyclopenta[a]indene-2-carboxylates and -ethanones (i.e., cyclopentenes) leads to 4a-phenyl-4b-R2-1,2,4a,4b,8b,8c-hexahydro-2-azabenzo[a]cyclopropa[cd]azulene-4-carboxylates and -ethanones (i.e., vinylcyclopropanes). The reverse transformation of compounds with vinylcyclopropyl moiety into...

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Section: Introductionmentioning

confidence: 99%

Switchable light vs. acid-induced transformations of complex framework compounds at room temperature

et al. 2022

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gem-Dichlorocyclopropanes and 1,3-Dioxacyclanes: Synthesis Based on Petroleum Products and Use in Low-Tonnage Chemistry

Raskil’dina,

Sultanova,

Zlotskii

2023

rev. and adv. in chem.

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Synthesis and reactions of alkenyl-gem-dichlorocyclopropanes obtained from piperylene

Musin

Borisova

Раскильдина

et al. 2020

Fine Chem. Technol.

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Objectives. This study aims to obtain alkenyl-gem-dichlorocyclopropanes from piperylene. The products are then subjected to thermocatalytic isomerization and hydrogenation.Methods. To determine the qualitative and quantitative composition of the reaction crudes, the following analytical methods were used: gas-liquid chromatography using the Crystal 2000 hardware complex, mass spectrometry using a Chromatec-Crystal 5000M device with the NIST 2012 database, and nuclear magnetic resonance (NMR) spectroscopy using a Bruker AM-500 device at operating frequencies of 500 and 125 MHz.Results. Alkenyl-gem-dichlorocyclopropanes were synthesized in the presence of triethylbenzyl ammonium chloride as catalyst. Their isomerization and hydrogenation gave the corresponding gem-dichlorocyclopentene and isomers of alkyl-gem-dichlorocyclopropanes. The structure of synthesized substances were analyzed by gas-liquid chromatography, mass spectrometry, and NMR spectroscopy.Conclusions. The results show that formation of four isomeric substituted gemdichlorocyclopropanes occurs in high yield during incomplete dichlorocyclopropanation of piperylene. The thermocatalytic isomerization of substituted gem-dichlorocyclopropanes in the presence of SAPO-34 zeolite leads to the formation of one product, i.e., gem-dichlorocyclopentene, and hydrogenation of substituted gem-dichlorocyclopropanes in the presence of Pd/C catalyst gives three isomeric alkyl-gem-dichlorocyclopropanes.

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Catalytic Isomerization of Substituted Vinylcyclopropanes

Cited by 3 publications

References 6 publications

Switchable light vs. acid-induced transformations of complex framework compounds at room temperature

Switchable light vs. acid-induced transformations of complex framework compounds at room temperature

gem-Dichlorocyclopropanes and 1,3-Dioxacyclanes: Synthesis Based on Petroleum Products and Use in Low-Tonnage Chemistry

Synthesis and reactions of alkenyl-gem-dichlorocyclopropanes obtained from piperylene

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