User:PME36/sandbox/Phenyl Sodium

Phenylsodium C6H5Na is an organometallic compound which can be used to phenylate ketones as well as alkyl, aryl, and acyl halides. The existence of phenylsodium was originally proposed by Kekulé after observing the formation of sodium benzoate in the reaction of bromobenzene with sodium under carbon dioxide. The solid compound was first isolated by Acree in 1903.

Transmetallation
In the original synthesis, diphenylmercury and sodium metal are heated in benzene to yield a suspension of phenylsodium.
 * (C6H5)2Hg  +  3 Na   &rarr;   2 C6H5Na  +  NaHg

Properties
n-Butylsodium has an ionic character, with a negative charge on the end carbon atom. n-Butylsodium is insoluble in saturated hydrocarbons, and reacts with unsaturated hydrocarbons. However it can be made to dissolve via the addition of coordinating compounds such as tetramethylethylenediamine or tetrahydrofuran.

Reactions
When n-butylsodium reacts with alkylbenzene or allylbenzene compounds, they become metalated, meaning that sodium is added. It adds to random positions on the ring or the side chain. This may not be the most stable compound, and the product may isomerise to move sodium to the side chain. When toluene reacts with n-butylsodium, the major product is benzylsodium.

n-Butylsodium can react with 1-bromonaphthalene to make 1-sodiumnapthalene and 1-bromobutane, but there are few such metathesis reactions.