Unexpected reaction of tellurium tetrachloride with allyltrimethylsilane

Мартынов, А. В.; Махаева, Н. А.; Ларина, Л. И.; Амосова, С. В.

doi:10.1134/s1070428011020230

Cited by 4 publications

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References 9 publications

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“…The formation of diallyltellurium dichloride (II) was confirmed by its 1 H and 125 Te NMR spectra which were fully identical to those reported in [7], as well as by its elemental composition. The 1 H NMR spectrum of compound II isolated from the reaction mixture by column chromatography contained only signals assignable to allyl group, whereas those typical of dimethylsilyl group were absent.…”

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confidence: 56%

“…However, Bergman et al [5] found that the addition of TeCl 4 to diallyl sulfide involves only one double bond according to Markovnikov, which was proved by the X-ray diffraction data. The reaction of TeCl 4 with 2 equiv of allyltrimethylsilane quantitatively yields diallyltellurium dichloride via 1,3-substitution of the silyl group and 1,2-migration of the double bond [6,7] due to β-effect of the trimethylsilyl group [8]. Reactions of TeCl 4 with diallylsilanes were not reported.…”

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confidence: 99%

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Reaction of tellurium tetrachloride with diallyldimethylsilane

2011

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Electrophilic Selenium/Tellurium Reagents: Reactivity and their Contribution to Green Chemistry

Santi

Tidei

2013

Patai's Chemistry of Functional Groups

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Selenium moieties are conveniently introduced into an organic molecule using electrophilic selenenylating reagents and the process is generally highly chemo‐, regio and stereoselective requiring mild experimental conditions. In addition, organoselenium derivatives can be directly converted into a number of different functional groups and the organoselenium moiety can be employed for further stereoselective manipulation of the molecule. Several applications are described for the inter‐ and intramolecular carbon–oxygen, carbon–nitrogen and carbon–carbon bond formation as well as for the α‐functionalization of carbonyl derivatives and the nucleophilic aromatic substitution reactions. More recently, the development of simple and efficient procedures for the preparation of chiral selenium reagents allowed their successful application in electrophilic asymmetric synthesis. Nowadays, probably the most recent aspect of this kind of chemistry is correlated with some new reactions that can be effected using organoselenium compounds as catalysts in renewable or alternative non‐toxic media (water, glycerol, ionic liquids) bringing this kind of research in line with the concept of ‘Green and Sustainable Chemistry’. During the last half century, the application of tellurium reagents has undergone a notable improvement, overcoming the reluctance of several researchers mainly due to the characteristic persistent smell of many tellurium derivatives. In this chapter some general aspects of the chemistry promoted by electrophilic selenium and tellurium compounds are described exploiting also the differences between these two reagents.

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