Magnesium_anthracene

Magnesium anthracene

Magnesium anthracene

Chemical compound

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]

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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

  1. [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. [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.
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