Synthesis and Stereochemistry of Optically Active Selenium and Tellurium Compounds

Kamigata, Nobumasa

doi:10.1080/10426500590907345

Cited by 4 publications

(3 citation statements)

References 32 publications

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“…In Figure 5.4, we illustrate the use of this nomenclature for ethylmethyphenyltelluronium ion. 18 For polyhedra larger than tetrahedrons, it is still the case that the clockwise or anticlockwise sequence of ligating atoms is used to define the chirality of the metal center, but it is now recommended to use the symbol C (clockwise) and A (anticlockwise) instead of R and S. The rules for determining ligand priority are unchanged. For the idealized structures with a single rotation axis, for example, trigonal bipyramidal (TBPY-5), see-saw (SS-4), square prismatic (SPY-5 and SPY-4), and octahedral (OC-6) structures with nonidentical monodentate ligands or one bidentate ligand, the unique reference axis coincides with the unique principal rotation axis.…”

Section: Nomenclature For Chiral Metal Complexesmentioning

confidence: 99%

“…For example, the role of chiral sulfur centers in biological processes has been reviewed recently, 91 and there have been a number of reports of the use of chiral phosphorus in asymmetric synthesis and toxicological studies. 92, 93 Kamigata has reviewed recent work on the chemistry of chiral selenium and tellurium compounds 18 ; chiral organotin compounds 94 are well known, and some stable compounds with chirality at the boron atom have been synthesized and exploited in asymmetric syntheses. 95,96 A number of interesting chiral structures are also known for boranes.…”

Section: Miscellaneous Inorganic Compoundsmentioning

confidence: 99%

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Absolute Chiral Structures of Inorganic Compounds

Riehl

Kaizaki

2010

Physical Inorganic Chemistry

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Chiral inorganic compounds play increasingly important roles in current research efforts concerned with asymmetric catalysis, biochemistry, and supramolecular chemistry. Although our ability to determine precise chiral structures of inorganic compounds and relate these structures to chemical phenomena is a relatively recent achievement, this area of research has been a central and fundamental subject since the beginning of modern chemistry. The realization that substances other than those containing tetrahedral carbon atoms could occur as nonsuperimposable mirrorimage forms was first made by the "father of coordination chemistry" Alfred Werner at the end of the nineteenth century. 1 A critical consequence of his octahedral coordination theory was that certain isomers of six-coordinate metal complexes should exist as enantiomeric pairs. As early as 1897, Werner was speculating on whether or not he could verify the existence of mirror-image compounds from sixcoordinate octahedral geometry, and the preparation and resolution of a chiral molecular metal complex was finally achieved by his research colleagues Ernst Scholze and Victor L. King with the publication of the separation of the optical isomers (enantiomers) of cis-bromoamminebis(ethylenediamine)cobalt(III) salts in 1911. 2 Figure 5.1 illustrates the structure of the two possible mirror-image structures for this complex. The separated complexes were shown to possess equal and opposite optical rotations (OR) confirming their mirror-image relationship. Alfred Werner received the Nobel Prize in Chemistry for his development of the coordination theory 2 years after the publication of this milestone work in 1913.Following the experimental results of Werner and his colleagues, a number of theoretical attempts were made to correlate the sign and magnitude of the optical rotation to the exact chiral molecular structure of metal complexes. These approaches have been summarized by Richardson. 3 The term "absolute structure" is sometimes limited to a discussion of the structure of noncentrosymmetric crystals, and the term Physical Inorganic Chemistry: Principles, Methods, and Models Edited by Andreja Bakac

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Section: Nomenclature For Chiral Metal Complexesmentioning

confidence: 99%

Section: Miscellaneous Inorganic Compoundsmentioning

confidence: 99%

Absolute Chiral Structures of Inorganic Compounds

Riehl

Kaizaki

2010

Physical Inorganic Chemistry

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“…For this molecule the SeSe rotational barrier is estimated at 8.2 kcal/mol through a synperiplanar and 5.2 kcal/mol through an antiperiplanar transition state. 5,6 The gauche conformation makes the diselenide chromophore inherently chiral. In the twisted diselenide chromophore, the HOMO energy level splits into the two n a and n b energy levels.…”

Section: Introductionmentioning

confidence: 99%

Helicity discrimination in diselenides by chiral substituents—a circular dichroism study

Skowronek

Ścianowski

Gawroński

2006

Tetrahedron: Asymmetry

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Functional Groups Containing Selenium and Tellurium in Oxidation States from 3 to 6

Kiełbasiński

Drabowicz

2011

Patai's Chemistry of Functional Groups

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The chapter presents the progress made in recent years (mostly after 1987) in the chemistry of the selenium and tellurium compounds in oxidation states from 3 to 6 but, to make the presentation more comprehensible, it also contains selected references to earlier achievements. It is divided into seven sections, comprising particular classes of organoselenium and organotellurium derivatives which are discussed in the order of increasing oxidation states: selenonium and telluronium salts, selenoxides, telluroxides, selenimines and tellurimines, selenones, tellurones and selenoximines. All the sections are divided into subsections devoted to the synthesis and structure, reactivity and transformations and synthetic applications of the discussed classes of compounds. Particular emphasis is laid on the synthesis and properties of the chiral, non‐racemic forms of each class of compounds.

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Synthesis and Stereochemistry of Optically Active Selenium and Tellurium Compounds

Cited by 4 publications

References 32 publications

Absolute Chiral Structures of Inorganic Compounds

Absolute Chiral Structures of Inorganic Compounds

Helicity discrimination in diselenides by chiral substituents—a circular dichroism study

Functional Groups Containing Selenium and Tellurium in Oxidation States from 3 to 6

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