Zinc Alkyls, Edward Frankland, and the Beginnings of Main-Group Organometallic Chemistry

Seyferth, Dietmar

doi:10.1021/om010439f

Cited by 138 publications

(162 citation statements)

References 106 publications

Supporting

Mentioning

157

Contrasting

Unclassified

Order By: Relevance

“…This phenomenon had already been recognized by Frankland and has plagued chemists ever since 25 . When it was recognized that 'ate' compounds often have enhanced reactivity and selectivity profiles compared to their parent organometallic compounds 26,27 , systematic studies of synthetic applications and structural features of organozincates started.…”

Section: A Introductionmentioning

confidence: 95%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

View full text Add to dashboard Cite

Section: A Introductionmentioning

confidence: 95%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

View full text Add to dashboard Cite

“…[1] Not only were they among the first organometallic compounds, but studies on their chemical reactions and vapor densities led to the first clear exposition of valency theory. [2] Since then both compounds have found widespread applications: They are important reagents in organic synthesis, [3] for example in the enantioselective alkylation of carbonyls [4] and imines [5] and in cyclopropanation reactions.…”

mentioning

confidence: 99%

The Solid‐State Structures of Dimethylzinc and Diethylzinc

Bacsa

Hanke

Hindley³

et al. 2011

Angewandte Chemie

View full text Add to dashboard Cite

Gut Ding braucht Weile: Mehr als 160 Jahre nach ihrer Entdeckung wurden nun die Festkörperstrukturen der klassischen metallorganischen Verbindungen Dimethylzink und Diethylzink mittels Röntgenkristallographie und Dichtefunktionalrechnung aufgeklärt. Zwischen den linearen Molekülen herrschen schwache intermolekulare Wechselwirkungen mit geringen kovalenten Anteilen. Me2Zn zeigt bei 180 K einen Übergang zwischen zwei festen Phasen (siehe Bild).

show abstract

“…It is worth mentioning here that disupersilylmetals (t-Bu 3 Si) 2 M, supersilylmetal halides (t-Bu 3 Si)MX and bis(disupersilyl)silylmetals [(t-Bu 3 Si) 2 SiH] 2 M (M = Zn, Cd, Hg; X = Cl, Br) have been recently prepared by reaction of the corresponding silyl-sodium salts with metal dihalides in 1:1 or 2:1 ratio, and could be fully characterized 23,24 (Scheme 3). The disupersilylzinc compound was found to react with BiCl 3 or BBr 3 to give the corresponding supersilylzinc halide (t-Bu 3 Si)ZnX.…”

Section: Alkylation Of Zinc Saltsmentioning

confidence: 99%

“…The driving force of the reaction is the formation of stable dialkylzinc compounds, and in some cases the formation of volatile organoboranes such as BMe 3 (bp = −22…”

Section: Boron -Zinc Exchangementioning

confidence: 99%

Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Gr��vy¹

2005

Encyclopedia of Inorganic Chemistry

View full text Add to dashboard Cite

Since the discovery of the first organozinc compounds by Sir Edward Frankland in 1849, the organometallic chemistry of zinc made remarkable advances and organozinc species have become essential tools for organic chemists. During the past decade, numerous new and modified procedures for the preparation of the title compounds have been published, rendering their synthesis easier, faster, and less expensive and giving higher yields. The coordination chemistry of organozinc derivatives has been subject of further interest and various intra‐ and intermolecular complexes with different donor ligands have been structurally characterized by X‐ray crystallography and spectroscopic methods. The accumulation of molecular structures, physicochemical studies, and computational calculations has led to a better understanding of the organozinc chemistry, and consequently to the design of new derivatives for specific applications. Even if the development of areas like the chemistry of organozinc anions and cations is still in its early stage, these compounds, which exhibit properties different than those of the parent organometallic species, appear to have promising applications in synthesis and catalytic reactions. During the past ten years, the chemistry of organo‐ gem ‐dizincio derivatives has also been the subject of much interest and progress. These reagents can form two carbon–carbon bonds in a one‐pot reaction and with high stereoselectivity. They became key reagents for organic chemists who want to combine multiple transformations in one operation. The importance of organometallic compounds of zinc can be seen in the growing number of their applications in synthesis. They are used in many reactions such as substitutions, additions to carbonyl compounds and unsaturated systems, cyclopropanations, and polymerizations. Furthermore, as a result of their low reactivity, they tolerate a wide variety of functionalities and perform most of the transformations with high regio‐ and enantioselectivity. After spending more than half a century in the shade of Grignard and organolithium reagents, organozinc reagents are becoming more and more important in modern chemistry.

show abstract

Zinc Alkyls, Edward Frankland, and the Beginnings of Main-Group Organometallic Chemistry

Cited by 138 publications

References 106 publications

Structural Organozinc Chemistry

Structural Organozinc Chemistry

The Solid‐State Structures of Dimethylzinc and Diethylzinc

Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Contact Info

Product

Resources

About