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Потапов, В. А.; Амосова, С. В.; Belozerova, O. V.; Albanov, A. I.; Yarosh, O. G.; Воронков, М. Г.

doi:10.1023/a:1024742119781

Cited by 47 publications

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“…We have earlier reported the addition reaction of selenium dichloride and dibromide to dimethyl diethynyl silane to give unsaturated 5-membered heterocycles [1,2]. The reaction was performed with various diorganyl diethynyl silanes and -germanes and provided previously unknown 1-selena-4-silafulvenes and 1-selena-4-germafulvenes [3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

“…In spite of the fact, that selenium dichloride and dibromide exist in equilibrium with other selenium species, these reagents can be used in reactions to give organoselenium compounds with good selectivity and in high yield [1][2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

“…As part of our continued investigations of reactions of selenium halides with organic compounds [1][2][3][4][5][6][7][8]13] we have recently studied the addition reaction of selenium dichloride (2) to divinyl sulfide (1) [14]. We found that the reaction at À50°C in chloroform afforded 2,6-dichloro-1,4-thiaselenane (3), in virtually quantitative yield (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

Потапов

Шагун

Пензик

et al. 2010

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

Потапов

Шагун

Пензик

et al. 2010

Journal of Organometallic Chemistry

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“…It is known that in solution selenium dibromide exists in equilibrium with Se 2 Br 2 and bromine [1]. We used the example of the addition of selenium dibromide to diethynyldimethylsilane to show for the first time that this reagent can be used in the synthesis of organoselenium compounds [2,3].We earlier found that selenium dichloride reacts with divinyl sulfide to form an unsaturated heterocycle, 2-chloromethyl-1,3-thiaselenol (yield 30%) which was isolated by distillation [4]. The reaction of selenium dibromide with divinyl sulfide have never been reported in the literature.…”

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confidence: 99%

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Reaction of selenium dibromide with divinyl sulfide

et al. 2009

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There are few data in the literature concerning reactions of selenium dibromide. It is known that in solution selenium dibromide exists in equilibrium with Se 2 Br 2 and bromine [1]. We used the example of the addition of selenium dibromide to diethynyldimethylsilane to show for the first time that this reagent can be used in the synthesis of organoselenium compounds [2,3].We earlier found that selenium dichloride reacts with divinyl sulfide to form an unsaturated heterocycle, 2-chloromethyl-1,3-thiaselenol (yield 30%) which was isolated by distillation [4]. The reaction of selenium dibromide with divinyl sulfide have never been reported in the literature.We found that the reaction of selenium dibromide with divinyl sulfide leads to an earlier unknown heterocyclic compound 5-bromo-2-bromomethyl-1,3-thiaselenolane (I) in 80% yield.Selenium dibromide was prepared in situ by the reaction of selenium with bromine in chloroform. Milne, J., Polyhedron, 1985, vol. 4, no. 1, p. 65. 2. Potapov, V.A., Amosova, S.V., Belozerova, O.V., Albanov, A. I., Yarosh, O.G., and Voronkov, M.G., Khim. Geterotsikl. Soedin., 2003, no. 4, p. 549. 3. Potapov, V.A. and Amosova, S.V., Zh. Org. Khim., 2003, vol. 39, no. 10, p. 1449. 4. Amosova, S.V., Penzik, M.V., Albanov, A.I., and Potapov, V.A., Izv. Akad. Nauk, Ser. Khim., 2008, no. 6, p. 1298 The reaction proceeds in chloroform at room temperature. Product I represents a mixture of diastereomers in a 3 : 2 ratio. 5-Bromo-2-bromomethyl-1,3-thiaselenolane (I).The structure of heterocycle I was established by 1 H, 13 C, and 77 Se NMR spectroscopy and confirmed by elemental analysis. It is a dark liquid which decomposes upon vacuum distillation.It can be assumed that the reaction of selenium dichloride with divinyl sulfide [4], too, involves initial formation of a saturated heterocycle, 5-chloro-2-chloromethyl-1,3-thiaselenolane, which undergoes subsequent dehydrochlorination to form 2-chloromethyl-1,3-thiaselenol.

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NMR of Organoselenium and Organotellurium Compounds

Panda

Singh

2012

Patai's Chemistry of Functional Groups

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This chapter gives a systematic account of and surveys the available data on 77 Se and 125 Te NMR spectra of organochalcogen compounds such as chacogenols, mono and dichalcogenides, chalcogenolates, tetra and hexa substituted chalcogen compounds, chalcogenyl halides, chalcogen‐containing heterocycles and macrocycles, chalcogen‐oxygen/nitrogen compounds, etc. The review is based on the literature from 1985 to 2011 and includes 780 references. The 77 Se/ 125 Te NMR spectra of organochalcogen compounds reveal expansive chemical shifts (δ Se /δ Te ) leading to sharp sensitivity of these nuclei (Se/Te) to their environment such as solvent, temperature, molecular geometry, ligand backbone, oxidation state, chelate ring size, steric strain, etc. This is well illustrated by the advantageous use of this spectroscopy in the successful determination of the solution state structure of several organochalcogen compounds. It is noted that the 125 Te and 77 Se chemical shifts of a large number of structurally similar organotellurium and selenium compounds show linear relationship.

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Cited by 47 publications

References 1 publication

Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

Reaction of selenium dibromide with divinyl sulfide

NMR of Organoselenium and Organotellurium Compounds

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