Cleavage of Tellurium-Carbon Bonds of Hexavalent Organotellurium Compounds by Potassium Graphite

Miyasato, Masataka; Minoura, Mao; Akiba, Kin‐ya

doi:10.1002/1521-3773(20010716)40:14<2674::aid-anie2674>3.0.co;2-h

Cited by 10 publications

(10 citation statements)

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“…Whereas cyclooctasulfur is the thermodynamically stable allotrope of the element at ambient conditions and the polymeric sulfur chain is unstable, polymeric tellurium is the only stable form of the element. (Me 3 Si) 3 CTeTe-TeC(SiMe 3 ) 3 11 or intramolecular heteroatom coordination. 3, secondary TeÁ Á ÁTe interactions (Section 4), as well as weaker bond energies and the increasing importance of hypervalency (Section 3) contribute to these differences.…”

Section: General Bonding Featuresmentioning

confidence: 99%

“…The tetrachalcogen tetranitrides E 4 N 4 (E = S, Se) both adopt an intriguing cage structure with two weak transannular EÁ Á ÁE interactions. diorganotellurium oxides R 2 TeO, diorganotellurones R 2 TeO 2 , organotellurinic acids RTe(O)OH, and organotelluronic acids RTe(O)(OH) 3 (Fig. 11).…”

Section: View Article Onlinementioning

confidence: 99%

“…The stabilisation of higher oxidation states is also a feature of organotellurium compounds, as illustrated by the existence of air-stable hexaaryltellurium compounds Ar 6 Te (Ar = Ph, 4-CF 3 C 6 H 4 ) and the related monoanions [Ar 5 Te] À , as well as Me 6 Te, 3 for which there are no lighter chalcogen analogues. However, as exemplified by the halides, higher oxidation states are more stable for selenium and, especially tellurium, in part as a result of lower ionization energies.…”

Section: Introductionmentioning

confidence: 99%

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Tellurium: a maverick among the chalcogens

2015

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The scant attention paid to tellurium in both inorganic and organic chemistry textbooks may reflect, in part, the very low natural abundance of the element. Such treatments commonly imply that the structures and reactivities of tellurium compounds can be extrapolated from the behaviour of their lighter chalcogen analogues (sulfur and selenium). In fact, recent findings and well-established observations clearly illustrate that this assumption is not valid. The emerging importance of the unique properties of tellurium compounds is apparent from the variety of their known and potential applications in both inorganic and organic chemistry, as well as materials science. With reference to selected contemporary examples, this Tutorial Review examines the fundamental concepts that are essential for an understanding of the unique features of tellurium chemistry with an emphasis on hypervalency, three-centre bonding, secondary bonding interactions, σ and π-bond energies (multiply bonded compounds), and Lewis acid behaviour.

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Section: General Bonding Featuresmentioning

confidence: 99%

Section: View Article Onlinementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tellurium: a maverick among the chalcogens

2015

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“…However, the situation was dramatically different for (4‐CF 3 C 6 H 4 ) 5 Te − K + C 8 , which could be methylated easily by CH 3 I 5e.…”

Section: Resultsmentioning

confidence: 98%

“…Although considerable attention has been paid to the hypervalency of some tetraorganotellurium compounds,3 of the hexavalent organotellurium compounds bearing more than five TeC bonds, (CH 3 ) 6 Te4 was the only structurally characterized compound until our recent reports 5. 6 We reported several new synthetic procedures for novel types of hexavalent organotellurium compounds bearing five or six TeC bonds; 1) first synthesis of (4‐CF 3 C 6 H 4 ) 6 Te ( 1 a ) by one‐pot reaction of 4‐CF 3 C 6 H 4 Li and TeCl 4 together with synthesis of Ph 6 Te ( 1 b ) by reaction of Ph 4 TeF 2 with PhLi,5a,b 2) Ph 5 TeCl ( 2 b ‐Cl) and Ph 5 TeBr ( 2 b ‐Br) by the reaction of SO 2 Cl 2 or Br 2, respectively, with Ph 5 Te − Li + generated from TeCl 4 or TeBr 4 with five equivalents of PhLi,5c,d 3) (4‐CF 3 C 6 H 4 ) 5 (CH 3 )Te ( 3 a ) from (4‐CF 3 C 6 H 4 ) 5 Te − K + C 8 by treatment with CH 3 I, 5e and 4) (4‐CH 3 C 6 H 4 ) 5 (CH 3 )Te ( 3 c ) from (4‐CH 3 C 6 H 4 ) 2 Te by treatment with KC 8 followed by reaction with CH 3 I 5f. These methods recently reported by us are illustrated in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Reactions of Hexavalent Organotellurium Compounds Bearing Five or Six TelluriumCarbon Bonds

Miyasato

Sagami

Minoura

et al. 2004

Chemistry A European J

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A variety of hexaorganotellurium compounds, Ar(6-n)(CH3)nTe [Ar=4-CF3C6H4, n=0 (1a), n=1 (3a), n=2 (trans-4a and cis-4a), n=3 (mer-5a), n=4 (trans-6a); Ph, n=0 (1b), n=1 (3b), n=2 (trans-4b); 4-CH3C6H4, n=0 (1c), n=1 (3c), n=2 (trans-4c), n=4 (trans-6c); 4-BrC6H4, n=0 (1d)] and Ar5(R)Te [Ar=4-CF3C6H4, R=4-CH3OC6H4 (8); Ar=4-CF3C6H4, R=vinyl (9), Ar=Ph, R=vinyl (10), Ar=4-CF3C6H4, R=PhSCH2 (11), Ar=Ph, R=PhSCH2 (12), Ar=4-CF3C6H4, R=nBu (13)] and pentaorganotellurium halides, Ar5TeX [Ar=4-CF3C6H4, X=Cl (2a-Cl), X=Br (2a-Br); Ar=Ph, X=Cl (2b-Cl), X=Br (2b-Br); Ar=4-CH3C6H4, X=Cl (2c-Cl), X=Br (2c-Br); Ar=4-BrC6H4, X=Br (2d-Br)] and (4-CF3C6H4)4(CH3)TeX [X=Cl (trans-7a-Cl) and X=Br (trans-7a-Br)] were synthesized by the following methods: 1) one-pot synthesis of 1 a, 2) the reaction of SO2Cl2 or Br2 with Ar5Te(-)Li+ generated from TeCl4 or TeBr4 with five equivalents of ArLi, 3) reductive cleavage of Ar(6-m)(CH3)(m)Te (m=0 or 2) with KC8 followed by treatment with CH3I, 4) valence expansion reaction from low-valent tellurium compounds by treatment with KC8 followed by reaction with CH3I, 5) nucleophilic substitution of Ar(6-y-z)(CH3)zTeX(y-z) (X=Cl, Br, OTf; z=0, 1; y=1, 2) with organolithium reagents. The scope and limitations and some details for each method are discussed and electrophilic halogenation of the hexaorganotellurium compounds is also described.

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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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Cleavage of Tellurium-Carbon Bonds of Hexavalent Organotellurium Compounds by Potassium Graphite

Cited by 10 publications

References 29 publications

Tellurium: a maverick among the chalcogens

Tellurium: a maverick among the chalcogens

Syntheses and Reactions of Hexavalent Organotellurium Compounds Bearing Five or Six TelluriumCarbon Bonds

NMR of Organoselenium and Organotellurium Compounds

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