Phenylcopper


Phenylcopper is an organometallic chemical compound of copper. Its chemical formula is, where copper is in the oxidation state of +1.

Synthesis

Phenylcopper was the first known organocopper compound and was first prepared in 1923 from phenylmagnesium iodide and copper iodide and in 1936 by Henry Gilman by transmetallation of phenylmagnesium iodide with copper chloride.
Phenylcopper can be obtained by reacting phenyl lithium with copper bromide in diethyl ether.

Properties

Phenylcopper is a colorless solid that is soluble in pyridine. It can be stored for a few days without decomposition under nitrogen or in vacuum. Rapid decomposition takes place in air. Water decomposes phenylcopper to form red copper oxide and varying amounts of benzene and biphenyl. It forms stable complexes with tributylphosphine and triphenylphosphine.
When dissolved in dimethyl sulfide, phenylcopper forms dimers and trimers.

Related structures

A diphenylcuprate ion exists that can form a salt with lithium, an example of a Gilman reagent.