Reaction of diselenium dichloride with acetylene

Мусалов, М. В.; Потапов, В. А.; Амосова, С. В.

doi:10.1134/s1070428011070232

Cited by 9 publications

(5 citation statements)

References 18 publications

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“…In order to obtain crystals suitable for X-ray analysis, the halogenation of selenides 7a,b and 8a,b, with bromine and sulfuryl chloride, was carried out. We found that the halogenation reaction Stereoselectivity of the addition of selenium halides to unsaturated compounds has been basically studied for acetylenes [45,[50][51][52][53][54][55][56]. The reactions of selenium dichloride and dibromide with acetylene occurred stereoselectively as anti-addition affording (E,E)-bis(2-halovinyl) selenides in high yields [50].…”

Section: Resultsmentioning

confidence: 99%

“…Efficient electrophilic selenium-containing reagents, selenium dichloride and dibromide, were first introduced in synthesis of organoselenium compounds in 2003 [15,16]. It has been demonstrated that selenium dichloride [17] and dibromide [15] (generated in situ from elemental selenium and sulfuryl chloride or bromine) can be successfully used for selective introduction of the selenium atom Stereoselectivity of the addition of selenium halides to unsaturated compounds has been basically studied for acetylenes [45,[50][51][52][53][54][55][56]. The reactions of selenium dichloride and dibromide with acetylene occurred stereoselectively as anti-addition affording (E,E)-bis(2-halovinyl) selenides in high yields [50].…”

Section: Introductionmentioning

confidence: 99%

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Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

et al. 2020

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The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr2 with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr2 and PhSeBr transfer reagents are Se(CH2CH2Br)2 and PhSeCH2CH2Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis(E-2-bromovinyl) selenides and unsymmetrical E-2-bromovinyl selenides was developed based on the SeBr2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr2 and PhSeBr to alkynes under the same conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

et al. 2020

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“…The passage of acetylene gas through a solution of Se2Cl2 in CCl4 under pressure (10-12 atm., 30- (2-chorovinyl)selenide in 98 % yield together with elemental selenium (eq.17) [65].…”

Section: Diselenium Dihalidesmentioning

confidence: 99%

Selenium– and tellurium–halogen reagents

Chivers

Laitinen

2018

Physical Sciences Reviews

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Abstract Selenium and tellurium form binary halides in which the chalcogen can be in formal oxidation states (IV), (II) or (I). They are versatile reagents for the preparation of a wide range of inorganic and organic selenium and tellurium compounds taking advantage of the reactivity of the chalcogen–halogen bond. With the exception of the tetrafluorides, the tetrahalides are either commercially available or readily prepared. On the other hand, the low-valent species, EX2 (E = Se, Te; X = Cl, Br) and E2X2 (E = Se, Te; X = Cl, Br) are unstable with respect to disproportionation and must be used as in situ reagents. Organoselenium and tellurium halides are well-known in oxidation states (IV) and (II), as exemplified by REX3, R2EX2 and REX (R = alkyl, aryl; E = Se, Te; X = F, Cl, Br, I); mixed-valent (IV/II) compounds of the type RTeX2TeR are also known. This chapter surveys the availability and/or preparative methods for these widely used reagents followed by examples of their applications in synthetic inorganic and organic selenium and tellurium chemistry. For both the binary halides and their organic derivatives, the discussion is subdivided according to the formal oxidation state of the chalcogen.

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“…Annulation reactions of selenium dihalides with unsaturated arenes gave various condensed heterocyclic compounds [ 40 , 41 , 42 , 43 , 44 ]. The addition of selenium dihalides to alkenes and alkynes afforded bis(2-haloalkyl) selenides [ 45 , 46 ] and bis(2-halovinyl) selenides in high yields [ 47 , 48 , 49 , 50 , 51 , 52 ]. Novel heterocycles [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 ] have been obtained by reactions of selenium dihalides with divinyl chalcogenides [ 63 , 64 , 65 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of a New Family of 2,6-Disulfanyl-9-selenabicyclo[3.3.1]nonanes

2021

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The efficient synthesis of a new family of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes in high yields has been developed based on 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion generated from bis-isothiouronium salt of 2,6-dibromo-9-selenabicyclo[3.3.1]nonane. The derivatives of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonane containing alkyl, allyl and benzyl moieties have been prepared in 90–99% yields by nucleophilic substitution of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion with alkyl, allyl and benzyl halides. The reaction of nucleophilic addition of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion to alkyl propiolates afforded 2,6-di(vinylsulfanyl)-9-selenabicyclo[3.3.1]nonanes. The conditions for regio- and stereoselective addition of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion to a triple bond of alkyl propiolates have been found. To date, not a single representative of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes has been described in the literature.

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Reaction of diselenium dichloride with acetylene

Cited by 9 publications

References 18 publications

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

Selenium– and tellurium–halogen reagents

Efficient Synthesis of a New Family of 2,6-Disulfanyl-9-selenabicyclo[3.3.1]nonanes

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