Organosodium chemistry

Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity. The principal organosodium compound of commercial importance is sodium cyclopentadienide. Sodium tetraphenylborate can also be classified as an organosodium compound since in the solid state sodium is bound to the aryl groups. Organometal bonds in group 1 are characterised by high polarity with corresponding high nucleophilicity on carbon. This polarity results from the disparate electronegativity of carbon (2.55) and that of lithium 0.98, sodium 0.93 potassium 0.82 rubidium 0.82 caesium 0.79). The carbanionic nature of organosodium compounds can be minimized by resonance stabilization, for example, Ph3CNa. One consequence of the highly polarized Na-C bond is that simple organosodium compounds often exist as polymers that are poorly soluble in solvents. In the original work the alkylsodium compound was accessed from the dialkylmercury compound by transmetallation. For example, diethylmercury in the Schorigin reaction or Shorygin reaction: (C2H5)2Hg + 2 Na → 2 C2H5Na + Hg The high solubility of lithium alkoxides in hexane is the basis of a useful synthetic route: LiCH2SiMe3 + NaO–t–Bu → LiOt–Bu + NaCH2SiMe3 For some acidic organic compounds, the corresponding organosodium compounds arise by deprotonation. Sodium cyclopentadienide is thus prepared by treating sodium metal and cyclopentadiene: 2 Na+ 2 C5H6 → 2 Na+ C5H5− + H2 Sodium acetylides form similarly. Often strong sodium bases are employed in place of the metal. Sodium methylsulfinylmethylide is prepared by treating DMSO with sodium hydride: CH3SOCH3 + NaH → CH3SOCHNa+ + H2 Trityl sodium can be prepared by sodium-halogen exchange: Ph3CCl + 2 Na → Ph3C− Na+ + NaCl Sodium also reacts with polycyclic aromatic hydrocarbons via one-electron reduction.

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Related concepts (7)

Alkylation

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins.

Organometallic chemistry

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well.