Stereospecific synthesis and crystal structure of the racemate of 1-thia-2-tellura-1(1-allyl-4-chloro)cyclopentane 2,2,2-trichloride

Bergman, Jan; Laitalainen, Tarja; Sundberg, Markku R.; Uggla, Rolf; Kivekäs, Raikko

doi:10.1016/s0277-5387(98)00080-1

Cited by 9 publications

(7 citation statements)

References 16 publications

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“…With monoallyl ethers and alcohols 1,2-addition occurs by Markownikoff rule, and with esters, amides, and iminoesters the 1,3-addition proceeds with the 1,2-migration of the acyloxy group [2,3]. Whereas in [4,5] it was stated that reactions of tellurium tetrahalogenides with diallyl ether, sulfi de, amines, and arylsulfamide proceeded as electrophilic anti-Markownikoff addition providing saturated sixmembered heterocycles, it was established in [6] by XRD analysis that the reaction of TeCl 4 with diallyl sulfi de in acetonitrile resulted in addition by Markownikoff rule to one double bond with the formation of 2,2,2-trichloride of 1-thia-2-tellura-1-(1-allyl-4-chloro)cyclopentane. The reactions of TeCl 4 with allylsilanes are unknown.…”

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confidence: 99%

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

et al. 2011

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confidence: 99%

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

et al. 2011

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“…Dimers formed by Ch⋅⋅⋅O ChBs trans to C are known for the selenium analogue of 1 b , [47] the corresponding arrangement for ( 1 X 2 ) 2 would be structure i. Structure ii would be assembled by two antiparallel Te⋅⋅⋅X ChBs, which are common in the crystals of organotellurium trihalides, R−TeX [48,49,58–62,50–57] . We used a combined experimental and computational approach to investigate the nature of the products of chlorination of 1 b and examine those issues.…”

Section: Methodsmentioning

confidence: 99%

“…Structure ii would be assembled by two antiparallel Te•••X ChBs, which are common in the crystals of organotellurium trihalides, RÀ TeX. [48,49,[58][59][60][61][62][50][51][52][53][54][55][56][57] We used a combined experimental and computational approach to investigate the nature of the products of chlorination of 1 b and examine those issues.…”

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confidence: 99%

Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso‐Tellurazole N‐Oxides

Lomax

Tomassetti

et al. 2021

Chemistry A European J

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Chlorination of 3-methyl-5-phenyl-1,2-tellurazole-2-oxide yielded the λ 4 Te dichloro derivative. Its crystal structure demonstrates that the heterocycle retains its ability to autoassociate by chalcogen bonding (ChB) forming macrocyclic tetramers. The corresponding Te•••O ChB distances are 2.062 Å, the shortest observed to date in aggregates of this type. DFTÀ D3 calculations indicate that while the halogenated molecule is stronger as a ChB donor it also is a weaker ChB acceptor; the overall effect is that the ChBs in the chlorinated homotetramer are not significantly stronger. However, partial halogenation or scrambling selectively yield the 2 : 2 heterotetramer with alternating λ 4 Te and λ 2 Te centers, which calculations identified as the thermodynamically preferred arrangement.Chalcogen bonding (ChB), [1][2][3][4][5][6][7] i. e. the attractive supramolecular interaction of electrophilic sites on atoms of heavy group 16elements (S, Se, Te) with electron-rich centers, has unveiled an array of fascinating chemistry in fields as diverse as Lewis-acid catalysis, [8][9][10][11][12][13][14][15] optical probes, [14,16,17] functional materials, [5,[18][19][20][21][22][23][24] crystal engineering, [25][26][27][28][29][30] ion recognition and transport, [22,[31][32][33][34][35][36] and protein folding. [37] Amongst the many molecules capable of forming ChBs, isotellurazole N-oxides (1, Scheme 1) stand apart because of their ability to spontaneously assemble cyclic tetramers (1 4 ) and hexamers (1 6 ) that exist in equilibrium in solution. [38][39][40] There are two electrophilic regions on the tellurium atom of 1, antipodal to each the NÀ Te and the CÀ Te bonds. The former has a larger V max and, consequently, the Te•••O ChB interaction in all known cases is formed trans to the N atom (e. g. 1 4,6 in Scheme 1). The Te•••O ChBs are reversible, scrambling is[a] P.

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“… (a) References[142,169,173,180,181,184,188–190,203,206,217,219,233,240,360–362,368,373,374,376,381,473,480,481,565–699 (b) References [260, 325, 381, 469, 700–729]. (c) References [730–732].…”

Section: Methodsmentioning

confidence: 99%

The Nature of the Chemical Bond in Linear Three-Body Systems: From I₃^–to Mixed Chalcogen/Halogen and Trichalcogen Moieties

Aragoni¹,

Arca²,

Devillanova³

et al. 2007

Bioinorganic Chemistry and Applications

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The 3 centre-4 electrons (3c-4e) and the donor/acceptor or charge-transfer models for the description of the chemical bond in linear three-body systems, such as I3 − and related electron-rich (22 shell electrons) systems, are comparatively discussed on the grounds of structural data from a search of the Cambridge Structural Database (CSD). Both models account for a total bond order of 1 in these systems, and while the former fits better symmetric systems, the latter describes better strongly asymmetric situations. The 3c-4e MO scheme shows that any linear system formed by three aligned closed-shell species (24 shell electrons overall) has reason to exist provided that two electrons are removed from it to afford a 22 shell electrons three-body system: all combinations of three closed-shell halides and/or chalcogenides are considered here. A survey of the literature shows that most of these three-body systems exist. With some exceptions, their structural features vary continuously from the symmetric situation showing two equal bonds to very asymmetric situations in which one bond approaches to the value corresponding to a single bond and the second one to the sum of the van der Waals radii of the involved atoms. This indicates that the potential energy surface of these three-body systems is fairly flat, and that the chemical surrounding of the chalcogen/halogen atoms can play an important role in freezing different structural situations; this is well documented for the I3 − anion. The existence of correlations between the two bond distances and more importantly the linearity observed for all these systems, independently on the degree of their asymmetry, support the state of hypervalency of the central atom.

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Stereospecific synthesis and crystal structure of the racemate of 1-thia-2-tellura-1(1-allyl-4-chloro)cyclopentane 2,2,2-trichloride

Cited by 9 publications

References 16 publications

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso‐Tellurazole N‐Oxides

The Nature of the Chemical Bond in Linear Three-Body Systems: From I₃^–to Mixed Chalcogen/Halogen and Trichalcogen Moieties

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Stereospecific synthesis and crystal structure of the racemate of 1-thia-2-tellura-1(1-allyl-4-chloro)cyclopentane 2,2,2-trichloride

Cited by 9 publications

References 16 publications

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso‐Tellurazole N‐Oxides

The Nature of the Chemical Bond in Linear Three-Body Systems: From I3–to Mixed Chalcogen/Halogen and Trichalcogen Moieties

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The Nature of the Chemical Bond in Linear Three-Body Systems: From I₃^–to Mixed Chalcogen/Halogen and Trichalcogen Moieties