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Magnesium anthracene

From Wikipedia, the free encyclopedia
Magnesium anthracene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.210.465Edit this at Wikidata
  • 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;3*1-2-4-6-5-3-1;/h1-10H;3*1-5H2;
    Key: RWNAQYFPPNXQES-UHFFFAOYSA-N
  • C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg]
  • 3 thf: C1CCOCC1.C1CCOCC1.C1CCOCC1.C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg]
Properties
C26H34MgO3
Molar mass418.860 g·mol−1
Appearanceorange solid
Density1.184 g/cm3
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Magnesium anthracene is anorganomagnesium compound that is almost invariably isolated as itsadduct with threetetrahydrofuran (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 ofanthracene.[1]

Structure and reactivity

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According toX-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, yieldingmagnesium hydride (MgH2).[1]

References

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  1. ^abBorislav 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.
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