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Потапов, В. А.; Амосова, С. В.; Belozerova, O. V.; Албанов, А. И.; Yarosh, O. G.; Воронков, М. Г.

doi:10.1023/a:1024794103851

Cited by 26 publications

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“…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].…”

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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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“…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%

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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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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“…1-3 The reaction of selenium tetra halides with acetylene affords bis(2 halovinyl)selenium dihalides. 4 We have previously 5, 6 studied the addition of the selenium tetra and dihalides to diethynyldimethyl silane. These reactions unexpectedly gave earlier un known heterocyclic systems: 3,6 dihalo 4,4 dimethyl 1,4 selenasilafulvenes 1a,b and 2,4 dihalo 2 dihalo methyl 3,3 dimethyl 1 selena 3 silacyclopent 4 enes (2a,b).…”

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Mass spectra of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes

et al. 2005

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The behavior of new heterocyclic systems, viz., 3,6 dihalo 4,4 dimethyl 1,4 selena silafulvenes 1а,b and 2,4 dihalo 2 dihalomethyl 3,3 dimethyl 1 selena 3 silacyclopent 4 enes 2a,b (Hal = Cl, Br), was studied under conditions of electron ionization and thermal decompo sition. Their fragmentation is accompanied by skeletal rearrangements, and the positive charge is localized mainly on ions containing silicon. Selenasilafulvenes 1a,b form stable molecular ions. Selenasilacyclopent 4 ene 2a decomposes partially and compound 2b decomposes com pletely in the gas phase with the elimination of a hydrogen halide and a halogen molecules.Key words: 3,6 dihalo 4,4 dimethyl 1,4 selenasilafulvene, 2,4 dihalo 2 dihalomethyl 3,3 dimethyl 1 selena 3 silacyclopent 4 ene, mass spectra, molecular ion, electron impact, frag mentation, rearrangement, elimination.Electrophilic addition of organylselenyl halides to acetylenes is the main method for the synthesis of 2 halovinyl selenides. 1-3 The reaction of selenium tetra halides with acetylene affords bis(2 halovinyl)selenium dihalides. 4 We have previously 5,6 studied the addition of the selenium tetra and dihalides to diethynyldimethyl silane. These reactions unexpectedly gave earlier un known heterocyclic systems: 3,6 dihalo 4,4 dimethyl 1,4 selenasilafulvenes 1a,b and 2,4 dihalo 2 dihalo methyl 3,3 dimethyl 1 selena 3 silacyclopent 4 enes (2a,b). X = Cl (a), Br (b)In continuation of these studies, 7 we studied the frag mentation of these compounds under electron ionization and showed that the character of their decomposition is determined by the size and saturation extent of the het erocycle and the nature of halogen and its position in the ring. 8 The compounds under study contain exocyclic halo gen atoms in both the heterocycle and side chain. In addition, the five membered unsaturated heterocycle con tains two endocyclic heteroatoms. Therefore, it seemed of interest to study specific features of the behavior of these compounds under electron ionization conditions. Upon electron ionization, halogen containing selena silafulvenes 1a,b form stable molecular ions, whose peaks are maximum. Their contributions* to the total ion cur rent are 23.2 and 32.2%, respectively. In both cases, an intense peak of the [М -Me] + ion (10.4 and 7.4%) is observed, which is characteristic of compounds contain ing the dimethylsilyl group. 9-14 Other fragmentation ions can be divided into two groups.The first group includes ions containing simultaneously halogen and silicon atoms: [MeSiX 2 ] + , [Me 2 SiX] + , [MeSi=С=CHX] + , and [SiX] + (X = Cl, Br). In the mass spectra of compounds 1a,b, the peaks of these rearrange ment ions are highly intense: their overall contribution to the total ion current is 27.4 and 31.5%, respectively (Table 1).Trimethylsilyl esters of haloalcohols and halogen substituted carboxylic acids 15 and halogen containing 2 silanocaranes 16 are characterized by skeleton rearrange ments caused by halogen atom migration to the silylic center. In this case, the bromodimethylsilyceni...

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Cited by 26 publications

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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

Mass spectra of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes

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