An organometallic compound is generally defined as one that possesses a metal carbon bond. It deals with molecules that contain a metal carbon bond. While many chemists prefer to say that for a compound to be classified as an organometallic compound, the type of metal carbon bonding in a molecule should be covalent or partially covalent in nature.
Based on periodic table one can broadly classify organometallic chemistry further into transition metal, main group metal and lanthanide/actinides based organometallics. Among these the most well developed, mechanistically understood and widely utilized in catalysis is transition metal organometallic chemistry.
Organometallic ReagentsBack to Top
Organosilicon protecting groups such as trimethylsilyl or tertiarybutyl dimethylsilyl and triisopropylsilyl also form an integral part of the organic chemists. Organic chemists use many organometallic reagents and catalysts for very specific applications. Some of the organometallic reagents are given below.
Organozinc compounds are much less nucleophilic than grignard reagents. The Reformatsky reaction which converts $\alpha$-haloesters and aldehydes to $\beta$-hydroxyesters also goes through an intermediate organozinc halide. In the Simmons-Smith reaction the carbenoid zinc iodide reacts with alkenes to form cyclopropanes.
The most useful organocopper reagents are lithium dialkylsuprates R2CuLi. These are formed by the reaction of two equivalents of an organolithium compound with a copper(I) halide.
The alkyl groups present in the organocadmium compounds are less nucleophilic than those in the organozinc compounds due to the general increase in electronegativity going down group 12.
The efficiency of the Fe(CO)3 moiety in protecting 1,3-dienes and its use as a stereo directing group in various types of reactions is well documented.
Inorganic chemists also explore the synthesis of new organometallic compounds their stability and structural studies and then determine their potential applications especially as catalysts.
Organometallic CatalystsBack to Top
|1||Dibutyltin dilaurate||Standard compound
|2||Stannous octoate ||Polysther-based slabstock foams|
|3||Dibutyltin diacetate |
|4||Dibutyltin dimercaptide |
|5||Lead naphthenate |
|7||Dibutyltin bis(4-hydroxyphenylacetate) |
|8||Dibutylin bis(2,3-dihydroxypropylmercaptide)||Hydrolytically stable|
|9||Ferric acetylacetonate||Elastomers |
Classical organometallic chemistry is typically non-aqueous. The water phase variants have prominently problems with the solubility of catalyst complexes. Organometallic catalysts frequently operate in zero oxidation state, which excludes the solubilizing action of ionization on the metal.
Organometallic SynthesisBack to Top
Synthesis of M-C containing compounds plays a central role in the field of organometallic chemistry. Both the metals and ligands are diverse. The former include those of main group, transition metals and lanthanide and actinide elements. The latter range from CO to multidentate organic molecules.
Since organometallic compounds contain metals and ligands the synthetic methods are in general grouped into two types.
- Reactions between metal species and preformed ligands or ligand precursors.
- Reactions of ligands in organometallic compounds yielding new ligands.
The former is used in the preparation of Grignard reagents, organolithium reagents and MeCo(CO)4. The latter is typified by the synthesis of Fischer carbene and carbyne complexes containing M=C and M triple bond C bonds. Some of the Organometallic Reactions are given below.
R-X + Mg $\rightarrow$ RMgX
MCl4 + 4LiCH2Bu $\rightarrow$ M(CH2BU)4 (M = Ti, Zr, Hf)
Na+[Co(CO)4]- + MeI $\rightarrow$ MeCo(CO)4
Organometallics CompoundsBack to Top
Grignard ReagentBack to Top
Grignard reagents possess significant nucleophilic character because of the highly polarized carbon-metal bond that results in considerable carbanionic character at carbon. Grignard reagents have found great utility and widespread use in organic synthesis.