Some free radical reactions of the allyl ester of 2-vinyl-2-methylcyclopropane-1-carboxylic acid

Guliev, A. M.; Ramazanov, G. A.; Gasanova, S. S.; Нефедов, О. М.

doi:10.1007/bf00960268

Cited by 2 publications

(2 citation statements)

References 2 publications

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“…To reveal the mechanism of radical homopolymerization of the synthesized unsaturated methylene dioxolanes 5-8 we have carried out the model reaction-addition of thiophenol (TPh) to these compounds. This reaction, first of all, makes it possible to determine the direction of attack of thiols radicals and to establish the microstructure of elementary links of the obtained polymers in their homopolymerization [5,6]. The addition reaction mechanism of TPh to the compounds 5-8 can be presented by the following scheme: The addition of TPh to the synthesized monomers 5-8 was carried out at 70 ºС in the presence of AIBN at various ratios of the initial reagents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Free-Radical Thiilation (Addition of Thiophenols) of Unsaturated Cyclic Acetals

Yusifli¹,

Ramazanov²,

Guliyev³

2019

JCCE

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The synthesis of a series of unsaturated 4-methylene-1,3-dioxolanes has been realized and the addition of thiophenol to the synthesized compounds in the presence of radical initiators has been carried out. It has been established the behavior of the addition reaction both with opening of dioxolane cycle and without it. The influence of nature of substituents of С 2-carbon atom of dioxolane cycle, ratio of the initial reagents and temperature on direction of the addition reaction has been studied. The adducts obtained as a result of the addition reaction have a linear and cyclic structure, which have been established by data of the chemical and spectral analyses. It has been found that the ratio dioxolane compound: thiophenol, reaction temperature and nature of the functional substituent influences on quantity of these adducts.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Free-Radical Thiilation (Addition of Thiophenols) of Unsaturated Cyclic Acetals

Yusifli¹,

Ramazanov²,

Guliyev³

2019

JCCE

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“…13 С NMR (CDCl 3 ), δ: 1.05, 1.30 (СН 2 СН 2 ); 16.49 (СН); 22.40 (Me); 34.40 (С(4)); 52.61, 52.65 (2 OMe); 96.68 (С(3)); 100.53 (С(5)); 170.65, 170.77 (2 COO). Dimethyl 1 cyclopropyl 2 methylcyclopropane 1,2 dicarb oxylate(10). Obtained in the preceding experiment reaction mixture (0.46 g) was heated in CHCl 3 (5 mL) at 50 °С for 1 h.After the solvent was evaporated by microdistillation in vacuo, a mixture of cis and trans isomers of dimethyl 1 cyclopropyl 2 methylcyclopropane 1,2 dicarboxylate (0.37 g, 92%) was iso lated in the ratio ~1 : 2.3, b.p.…”

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confidence: 99%

Synthesis and chemical transformations of 2-cyclopropyl-2-diazoacetates

et al. 2007

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Methyl 2 cyclopropyl 2 diazoacetate was synthesized from acetylcyclopropane in few chemical steps in ~55% total yield. Its copper or rhodium catalyzed dediazoniation exclusively proceeds through the intramolecular isomerization of generated cyclopropyl(methoxy carbonyl)carbene to 1 methoxycarbonylcyclobutene, irrespective of the presence or the ab sence of unsaturated compounds. However, in the presence of acrylates or strained cycloalkenes, this diazo ester is being slowly involved into the 1,3 dipolar cycloaddition, giving cyclopropyl substituted pyrazolinecarboxylates, which in case of 1 pyrazolines easily lose nitrogen mol ecule to selectively afford 1 cyclopropylcyclopropanecarboxylate derivatives.

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Some free radical reactions of the allyl ester of 2-vinyl-2-methylcyclopropane-1-carboxylic acid

Cited by 2 publications

References 2 publications

Synthesis and Free-Radical Thiilation (Addition of Thiophenols) of Unsaturated Cyclic Acetals

Synthesis and Free-Radical Thiilation (Addition of Thiophenols) of Unsaturated Cyclic Acetals

Synthesis and chemical transformations of 2-cyclopropyl-2-diazoacetates

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