User:PME36/sandbox/Phenyl Sodium

Phenylsodium
Names
	Other names Sodium benzenide, Sodium phenyl
Identifiers
CAS Number	1623-99-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	9183013 ;
PubChem CID	11007827;
	InChI InChI=1S/C6H5.Na/c1-2-4-6-5-3-1;/h1-5H;/q-1;+1 Key: KSMWLICLECSXMI-UHFFFAOYSA-N;
	SMILES C1=CC=[C-]C=C1.[Na+];
Properties
Chemical formula	C6H5Na
Molar mass	100.096 g·mol−1
Appearance	Yellowish-white powder
Solubility in water	Reacts
Solubility	Insoluble in hydrocarbons, reacts with ether
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Corrosive, pyrophoric in air
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

Synthesis

Transmetallation

In the original synthesis, diphenylmercury and sodium metal are heated in benzene to yield a suspension of phenylsodium.

(C₆H₅)₂Hg + 3 Na → 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.^[1] However it can be made to dissolve via the addition of coordinating compounds such as tetramethylethylenediamine or tetrahydrofuran.^[2]

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.^[3]

n-Butylsodium can react with 1-bromonaphthalene to make 1-sodiumnapthalene and 1-bromobutane,^[4] but there are few such metathesis reactions.^[5]

References

^ Coates, G. E. (2012). Principles of Organometallic Chemistry. Springer Science & Business Media. p. 50. ISBN 9789401096812.
^ Cite error: The named reference schade was invoked but never defined (see the help page).
^ Broaddus, C. D. (September 1966). "Metalation of Toluene. The Question of Kinetic vs. Thermodynamic Control". Journal of the American Chemical Society. 88 (18): 4174–4178. doi:10.1021/ja00970a012.
^ Gilman, Henry; Moore, Fred W.; Baine, Ogden (September 1941). "Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them". Journal of the American Chemical Society. 63 (9): 2479–2482. doi:10.1021/ja01854a046.
^ Schlosser, M. (April 1964). "Organosodium and Organopotassium Compounds Part I: Properties and Reactions" (PDF). Angewandte Chemie International Edition in English. 3 (4): 287–306. doi:10.1002/anie.196402871.

Category:Organosodium compounds

[1] Coates, G. E. (2012). Principles of Organometallic Chemistry. Springer Science & Business Media. p. 50. ISBN 9789401096812.

[schade-2] Cite error: The named reference schade was invoked but never defined (see the help page).

[3] Broaddus, C. D. (September 1966). "Metalation of Toluene. The Question of Kinetic vs. Thermodynamic Control". Journal of the American Chemical Society. 88 (18): 4174–4178. doi:10.1021/ja00970a012.

[4] Gilman, Henry; Moore, Fred W.; Baine, Ogden (September 1941). "Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them". Journal of the American Chemical Society. 63 (9): 2479–2482. doi:10.1021/ja01854a046.

[5] Schlosser, M. (April 1964). "Organosodium and Organopotassium Compounds Part I: Properties and Reactions" (PDF). Angewandte Chemie International Edition in English. 3 (4): 287–306. doi:10.1002/anie.196402871.

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