Reactions of 1,2‐Dihaloethanes with Chalcogenide Anions.

Russavskaya, N. V.; Grabel’nykh, V. A.; Леванова, Е. П.; Sukhomazova, E. N.; Клыба, Л. В.; Zhanchipova, E. R.; Татаринова, А. А.; Elaev, A. V.; Deryagina, É. N.; Корчевин, Н. А.

doi:10.1002/chin.200643057

ChemInform

2006

DOI: 10.1002/chin.200643057

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Reactions of 1,2‐Dihaloethanes with Chalcogenide Anions.

N. V. Russavskaya

V. A. Grabel’nykh

Е. П. Леванова

et al.

Abstract: Thioethers P 0430Reactions of 1,2-Dihaloethanes with Chalcogenide Anions. -Reaction of dichloroethane (I) with the anions , and in the system KOH-hydrazine hydrate proceeds with ethylene evolution and chalcogen regeneration. Only the reaction with the , or Me-Seanions generates oligomers which on hydrazine reduction furnish the expected dithio (seleno)ethane derivatives (III), (IV) and (VI). -(RUSSAVSKAYA, N. V.; GRABEL'NYKH, V. A.; LEVANOVA, E. P.; SUKHOMAZOVA, E. N.; KLYBA, L. V.; ZHANCHIPOVA, E. R.; TATARIN… Show more

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“…The chemical properties of 1,2-ditellurolane was not mentioned in these papers. We recently developed a method for the synthesis of 1,2-dithiolane [16] and 1,2-diselenolane [17] based on the activation of sulfur or selenium in a hydrazine hydrate-alkali system. The reaction of tellurium with 1-bromo-3-chloropropane was carried out in this system.…”

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1,2-Ditellurolane: A new synthetic method, structure and chemical reactions

Russavskaya

Elaev

Grabel’nyh

et al. 2006

Chem Heterocycl Compd

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A simple method for the synthesis of 1,2-ditellurolane is proposed, based on the reaction of elemental tellurium with 1,3-dihalopropane in a system of hydrazine hydrate and alkali followed by the effect of organic solvent on the first formed poly(trimethyleneditellurides). The products of the oxidation and reduction of 1,2-ditellurolane were characterized and its spectral characteristics were analyzed.The reaction of elemental sulfur with alkenylbenzenes, leading to the formation unique heterocyclic compounds -phenyl-substituted 1,2-dithiole-3-thiones -was discovered by M. G. Voronkov in the middle of the last century [1][2][3][4]. Then under his quindance 1,2-dithiol-3-one [5] and 1,2-diselenol-3-one [6] were prepared. This made possible the development of the synthetic chemistry of heterocycles with two chalcogen atoms which possess aromatic properties. Many of these or their derivatives were used in organic synthesis [7] and also as biologically active compounds [8] or industrial products [9].Saturated heterocyclic systems containing two chalcogen atoms (1,2-dichalcogenolans) have been far less studied. This is explained by the difficulty of making and separating them, especially the selenium and tellurium analogs. A multistage synthesis of 1,2-diselenolane has been described using potassium cyanide [10] or metallic lithium [11]. This compound has found use in organic synthesis, for example, in the preparation of stable cross-linked cyclodextrins with selenium bridges with hydrophobic cavities which are able to form inclusion complexes [12], and also calixarenes containing selenium [13]. The preparation of 1,2-ditellurolane 1 was first reported in 1984 [14]. It was obtained by the reaction of 1,3-dibromopropane with polytelluride anions generated by electrochemical reduction of tellurium and was characterized by UV spectroscopy and mass spectrometry. Subsequently 1,2-ditellurolane was obtained by cyanide activation of tellurium followed by reaction with 1,3-dibromopropane [15]. The product was only characterized in solution. The chemical properties of 1,2-ditellurolane was not mentioned in these papers. _______ * Dedicated to Academician of the Russian Academy of Science Mikhail Grigor'evich Voronkov on his 85 th Birthday. __________________________________________________________________________________________

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confidence: 99%

1,2-Ditellurolane: A new synthetic method, structure and chemical reactions

Russavskaya

Elaev

Grabel’nyh

et al. 2006

Chem Heterocycl Compd

Self Cite

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Reactions of 1,2‐Dihaloethanes with Chalcogenide Anions.

Cited by 1 publication

References 1 publication

1,2-Ditellurolane: A new synthetic method, structure and chemical reactions

1,2-Ditellurolane: A new synthetic method, structure and chemical reactions

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