Lead structures in lithium organic chemistry

Stey, Thomas; Stalke, Dietmar

doi:10.1002/047002111x.ch2

Cited by 107 publications

(54 citation statements)

References 251 publications

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“…[10,11] This avoids the unfavoured threefold coordination at the lithium centre. The anionic charge is delocalised over the aromatic system, which is also indicated by a short C ipso ÀC a bond length of 1.419(5) and 1.417(5) and the angular sum at C a of 357(4)8 and 357(3)8, in diastereomer one and two, respectively.…”

Section: Resultsmentioning

confidence: 99%

A Route to Stereochemically Pure Benzyllithium Reagents by Stereocontrolled Epimerisation

Koller

Kroesen

Strohmann

2014

Chemistry A European J

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Alkyllithium compounds are not generally stable at room temperature, therefore strategies were established to overcome this limitation. We present a systematic approach to obtain a stereochemically enriched benzyllithium compound, starting with the simple addition of a chiral auxiliary and ending by incorporation of the auxiliary in the substrate. Thereby, a very unusual dimer of a lithiated benzylsilane was obtained, which could be split into stereochemically enriched monomers by the addition of Lewis bases. Furthermore, we were able to understand the factors responsible for this stereochemical enrichment by using quantum chemical calculations and clarify the configuration of the lithiated compound and the corresponding trapping product by crystallisation. This enabled us to determine the stereochemical course of the deprotonation and the subsequent metathesis reaction.

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Section: Resultsmentioning

confidence: 99%

A Route to Stereochemically Pure Benzyllithium Reagents by Stereocontrolled Epimerisation

Koller

Kroesen

Strohmann

2014

Chemistry A European J

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“…The coordination of a carbanion to a Li 3 triangle, [109] a structural motif wellknown throughout organolithium chemistry, is also present…”

Section: Sulfur-diimide S(nr) 2 and Sulfur-triimide S(nr)mentioning

confidence: 99%

Meaningful Structural Descriptors from Charge Density

Stalke

2011

Chemistry A European J

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144

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This paper provides a short introduction to the basics of electron density investigations. The two predominant approaches for the modelling and various interpretations of electron density distributions are presented. Their potential translations into chemical concepts are explained. The focus of the article lies on the deduction of chemical properties from charge density studies in some selected main group compounds. The relationship between the obtained numerical data and commonly accepted simple chemical concepts unfortunately is not always straightforward, and often the chemist relies on heuristic connections rather than rigorously defined ones. This article tries to demonstrate how charge density analyses can shed light on aspects of chemical bonding and reactivity resulting from the determined bonding situation. Sometimes this helps to identify misconceptions and sets the scene for new unconventional synthetic approaches.

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“…During these studies, 71 was obtained as a crystalline material and its structure in the solid state was established by an X-ray crystal structure determination 126 . In 71 the two benzoyloxymethyl groups are symmetry-related via an inversion centre at the zinc position (7) • and C(1)−Zn−O(2) 113.53 (8) • ] point to a distorted squarebipyramidal environment at zinc.…”

Section: Diorganozinc Compounds Containing Intramolecularly Coordimentioning

confidence: 99%

“…Methylzinc isopropyl sulfide is an octamer (MeZnSPr-i) 8 in which all the sulfide groups are µ 3 -bridge-bonded to three zinc atoms, rendering them all distorted tetrahedral. No further details are given for this structure.…”

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 99%