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Concept
Organocopper chemistry
Summary
Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. They are reagents in organic chemistry.
The first organocopper compound, the explosive copper(I) acetylide (), was synthesized by Rudolf Christian Böttger in 1859 by passing acetylene gas through a solution of copper(I) chloride:
Organocopper compounds are diverse in structure and reactivity, but almost all are based on copper with anoxidation state of +1, sometimes denoted Cu(I) or . With 10 electrons in its valence shell, the bonding behavior of Cu(I) is similar to Ni(0), but owing to its higher oxidation state, it engages in less pi-backbonding. Organic derivatives of copper's higher oxidation states +2 and +3 are sometimes encountered as reaction intermediates, but rarely isolated or even observed.
Organocopper compounds form complexes with a variety of soft ligands such as alkylphosphines (), thioethers (), and cyanide ().
Due to the spherical electronic shell of , copper(I) complexes have symmetrical structures - either linear, trigonal planar or tetrahedral, depending on the number of ligands.
Copper(I) salts have long been known to bind CO, albeit weakly. A representative complex is CuCl(CO), which is polymeric. In contrast to classical metal carbonyls, pi-backbonding is not strong in these compounds.
Alkenes bind to copper(I), although again generally weakly. The binding of ethylene to Cu in proteins is of broad significance in plant biology so much so that ethylene is classified as a plant hormone. Its presence, detected by the Cu-protein, affects ripening and many other developments.
Although copper does not form a metallocene, half-sandwich complexes can be produced. One such derivative is π-cyclopentadienyl(triethylphosphine)copper(I).
Copper halides react with organolithium reagents to give organocopper compounds. The area was pioneered by Henry Gilman, who reported methylcopper in 1936.
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