Magnesium anthracene

Magnesium anthracene
Identifiers
CAS Number	86901-19-1;
3D model (JSmol)	Interactive image; 3 thf: Interactive image;
ChemSpider	3 thf: 9038788;
ECHA InfoCard	100.210.465
PubChem CID	21928237 with charge error; 3 thf: 10863500;
	InChI InChI=1S/C14H10.Mg/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1;/h1-10H;/q;+2 Key: UUHXXHJSGPKOGI-UHFFFAOYSA-N; 3 thf: InChI=1S/C14H10.3C5H10O.Mg/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1;31-2-4-6-5-3-1;/h1-10H;31-5H2; Key: RWNAQYFPPNXQES-UHFFFAOYSA-N;
	SMILES C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg]; 3 thf: C1CCOCC1.C1CCOCC1.C1CCOCC1.C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg];
Properties
Chemical formula	C26H34MgO3
Molar mass	418.860 g·mol−1
Appearance	orange solid
Density	1.184 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Magnesium anthracene is an organomagnesium compound that is almost invariably isolated as its adduct with three tetrahydrofuran (thf) ligands. With the formula Mg(C₁₄H₁₀)(thf)₃, this air- and water-sensitive orange solid is obtained by heating a suspension of magnesium in a thf solution of anthracene.[1]

Structure and reactivity

According to X-ray crystallography, the Mg center is 5-coordinate, occupying a C₂O₃ ligand sphere. The fold angle between the two benzo groups is 72.6°.[2]

The compound behaves as a source of the carbanion [C₁₄H₁₀]^2- as well as a source of highly reactive Mg. With electrophiles, the compound reacts to give dihydroanthracene derivatives C₁₄H₁₀E₂. Electrophiles include ketones, CO₂, organotin chlorides, and organoaluminium chlorides. Ethylene inserts into one Mg-C bond. Hydrogen induces release of anthracene, yielding magnesium hydride (MgH₂).[1]

References

Borislav Bogdanovic (1988). "Magnesium Anthracene Systems and Their Application in Synthesis and Catalysis". Accounts of Chemical Research. 21 (7): 261–267. doi:10.1021/ar00151a002.
L. M. Engelhardt; S. Harvey; C. L. Raston; A. H. White (1988). "Organomagnesium Reagents: The Crystal Structures of [Mg(anthracene)(THF)₃] and [Mg(triphenylmethyl)Br(OEt₂)₂]". Journal of Organometallic Chemistry. 341 (1–3): 39. doi:10.1016/0022-328X(88)89061-2.

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[Bogdan-1] Borislav Bogdanovic (1988). "Magnesium Anthracene Systems and Their Application in Synthesis and Catalysis". Accounts of Chemical Research. 21 (7): 261–267. doi:10.1021/ar00151a002.

[2] L. M. Engelhardt; S. Harvey; C. L. Raston; A. H. White (1988). "Organomagnesium Reagents: The Crystal Structures of [Mg(anthracene)(THF)₃] and [Mg(triphenylmethyl)Br(OEt₂)₂]". Journal of Organometallic Chemistry. 341 (1–3): 39. doi:10.1016/0022-328X(88)89061-2.