N-Butylsodium

"n"-Butylsodium CH3CH2CH2CH2Na is an organometallic compound with the idealized formula NaC4H9. Like other simple organosodium compounds, it is polymeric and highly basic. In contrast to "n"-butyllithium, "n"-butylsodium is only of specialized academic interest.
Preparation.
"n"-Butylsodium is prepared from "n"-butyllithium and "t"-butoxysodium.
Properties.
In "n"-Butylsodium, the Na-C bond has ionic character, with a negative charge on the end carbon atom. "n"-Butylsodium is insoluble in saturated hydrocarbons. It reacts with unsaturated hydrocarbons. Soluble adducts are produced with Lewis bases such as tetramethylethylenediamine or tetrahydrofuran.
Reactions.
"n"-Butylsodium reacts with alkylbenzene or allylbenzene compounds to give new organosodium compounds. With toluene the major product is benzylsodium.
"n"-Butylsodium reacts with 1-bromonaphthalene to make 1-sodiumnapthalene and 1-bromobutane, but there are few such metathesis reactions.