Reaction of 1-bromo-3-chloropropane with tellur and dimethyltelluride in the system of hydrazine hydrate-alkali

Russavskaya, N. V.; Леванова, Е. П.; Sukhomazova, E. N.; Grabel’nykh, V. A.; Elaev, A. V.; Клыба, Л. В.; Zhanchipova, E. R.; Albanov, A. I.; Korotaeva, I. M.; Totyashinova, D. S.; Корчевин, Н. А.

doi:10.1134/s1070363206050112

Cited by 12 publications

(2 citation statements)

References 9 publications

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“…We prepared tellurium-containing oligomers with paramagnetic properties [4] from 1-bromo-3-chloropropane [5] and chlorex [6]. However, in the reaction of 1,2-dihaloethanes with tellurium (or selenium) under similar conditions no oligomeric products are formed, but rather dehalogenation with the evolution of ethylene and elemental chalcogens is observed [7].…”

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Synthesis and reductive splitting of tellurium-containing oligomers on the basis of 1-bromo-2-methyl-3-chloropropane

et al. 2012

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The results of the synthesis of tellurium-containing oligomers based on 1-bromo-2-methyl-3-chloropropane are presented. By the example of the reductive splitting of tellurocol the possibility is demonstrated of the synthesis of methyltellanyl derivatives, which are valuable reagents for organic synthesis and for the design of coordination compounds.Polymers and oligomers containing tellurium atoms in the chain possess a number of practically valuable properties [1]. Generally, they are synthesized by polycondensation of organic dihalogenides with polytellurides of alkali metals M 2 Те n (M = Na, K; n = 1-3), which, in turn, are prepared from elemental tellurium in the redox systems [2]. By using such an approach, polyaryleneditellurides have been prepared [3].We prepared tellurium-containing oligomers with paramagnetic properties [4] from 1-bromo-3-chloropropane [5] and chlorex [6]. However, in the reaction of 1,2-dihaloethanes with tellurium (or selenium) under similar conditions no oligomeric products are formed, but rather dehalogenation with the evolution of ethylene and elemental chalcogens is observed [7]. A similar course of the reaction, that is, elimination of the vicinal halogen atoms (as halogenide anions) under the action of soft nucleophiles, in particular, chalcogen-containing, is a well-known reaction [8] proceeding, as many authors believe, as a halogenophilic attack of the nucleophile at the halogen atom [9]. The halogenophilic attack and the subsequent elimination of the halogen, in turn, are to a considerable extent determined by steric effects caused by the vicinal arrangement of the halogen atoms.In some cases the elimination of halogens may occur also with the derivatives of 1,3-dihalopropanes. Thus, the course of the reaction of 1,3-dibromo-and 1,3-dichloropropane with RTeLi (R = Me, Ph) depends on the temperature: at -196°С the substitution of the halogen atoms by RTe is observed, whereas at 25°С, the formation of propene and R 2 Te 2 [10]. The reaction of МеTeLi with tetrakis(bromomethyl)methane, in which the bromine atoms are in the 1,3-position to each other, the substitution of two bromine atoms by the methyltellanyl group is observed with elimination of the other two bromine atoms and the formation of the cyclopropane derivative [10].1-Bromo-2-methyl-3-chloropropane (I) has the methyl group in the vicinal position with respect to the halogen atoms. The methyl group is sterically equivalent to the bromine atom [11], so, it can create steric hindrances to conventional nucleophilic substitution and favor the halogenophilic attack and elimination of the halogen atoms.We have performed the reaction of dihalogenide I with elemental tellurium in the system hydrazine hydrate-KОН, in which tellurium suffers reductive activation with the formation of potassium telluride

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“…When the temperature of the reaction was 50-55°С, no products of elimination (methylpropene or methylcyclopropane) were detected. and seven-membered rings, for example, from chlorex, are formed rather easily under proper conditions [5].…”

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Synthesis and reductive splitting of tellurium-containing oligomers on the basis of 1-bromo-2-methyl-3-chloropropane

et al. 2012

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Organic Diselenides, Ditellurides, Polyselenides and Polytellurides. Synthesis and Reactions

Потапов¹

2013

Patai's Chemistry of Functional Groups

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Organic diselenides and ditellurides represent very important classes of compounds, which find valuable applications in organochalcogen chemistry and in organic synthesis. The review describes the main efficient and reliable approaches to organic diselenides and ditellurides and their principal chemical reactions. Examples of syntheses of tri‐ and polyselenides and ‐tellurides have been presented. Typical reactions of organic diselenides and ditellurides with nucleophiles, electrophiles, radicals, carbenes and compounds containing the element‐element bond have been discussed in the review. Regio‐ and stereoselective reactions of organic diselenides and ditellurides with unsaturated compounds provide various chalcogenyl and bis(chalcogenyl) derivatives, which are often used in further transformations including stereoselective synthesis of functionalized alkenes. Along with valuable chemical reactions, organic diselenides and ditellurides act as precursors of both nucleophilic and electrophilic selenium and tellurium species, which participate in various useful transformations. The remarkable property of reacting with high regio‐ and stereoselectivity finds widespread application of selenium and tellurium species in organic synthesis. Besides valuable synthetic applications, organic diselenides and ditellurides exhibit various biological activities including glutathione peroxidase‐like action. Aspects of biological activity of these compounds as well as a comparison of selenol–diselenide and thiol–disulfide reversible exchange reactions have been discussed in the review.

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Cyclocondensation of dichloroethenes with alkanedichalcogenolates in the hydrazine hydrate – alkali system. The synthesis of dihydrodithiine and trihydrodichalcogenepines

Rosentsveig,

Grabelnykh,

Bogdanova

et al. 2024

Chem Heterocycl Comp

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Reaction of 1-bromo-3-chloropropane with tellur and dimethyltelluride in the system of hydrazine hydrate-alkali

Cited by 12 publications

References 9 publications

Synthesis and reductive splitting of tellurium-containing oligomers on the basis of 1-bromo-2-methyl-3-chloropropane

Synthesis and reductive splitting of tellurium-containing oligomers on the basis of 1-bromo-2-methyl-3-chloropropane

Organic Diselenides, Ditellurides, Polyselenides and Polytellurides. Synthesis and Reactions

Cyclocondensation of dichloroethenes with alkanedichalcogenolates in the hydrazine hydrate – alkali system. The synthesis of dihydrodithiine and trihydrodichalcogenepines

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