(Cymene)ruthenium dichloride dimer

(Cymene)ruthenium dichloride dimer is the organometallic compound with the formula [(cymene)RuCl2]2. This red-coloured, diamagnetic solid is a reagent in organometallic chemistry and homogeneous catalysis. The complex is structurally similar to (benzene)ruthenium dichloride dimer.

(cymene)ruthenium dichloride dimer
Names
Other names
Dichloro(p-cymene)ruthenium(II) dimer
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.103.371
  • InChI=1S/2C10H14.4ClH.2Ru/c2*1-8(2)10-6-4-9(3)5-7-10;;;;;;/h2*4-8H,1-3H3;4*1H;;/q;;;;;;2*+2/p-4 checkY
    Key: LAXRNWSASWOFOT-UHFFFAOYSA-J checkY
  • InChI=1/2C10H14.4ClH.2Ru/c2*1-8(2)10-6-4-9(3)5-7-10;;;;;;/h2*4-8H,1-3H3;4*1H;;/q;;;;;;2*+2/p-4
    Key: LAXRNWSASWOFOT-XBHQNQODAM
  • [Ru+2].[Ru+2].[Cl-].[Cl-].[Cl-].[Cl-].c1cc(ccc1C(C)C)C.c1cc(ccc1C(C)C)C
  • Cc1ccc(cc1)C(C)C.Cc1ccc(cc1)C(C)C.[Cl-].[Cl-].[Cl-].[Cl-].[Ru+2].[Ru+2]
Properties
C20H28Cl4Ru2
Molar mass 612.38 g·mol−1
Appearance Red solid
Melting point 247 to 250 °C (477 to 482 °F; 520 to 523 K) (decomposes)
Slightly, with hydrolysis
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation and reactions

The dimer is prepared by the reaction of the phellandrene with hydrated ruthenium trichloride.[1] At high temperatures, [(cymene)RuCl2]2 exchanges with other arenes:

[(cymene)RuCl2]2 + 2 C6Me6 → [(C6Me6)RuCl2]2 + 2 cymene

(Cymene)ruthenium dichloride dimer reacts with Lewis bases to give monometallic adducts:

[(cymene)RuCl2]2 + 2 PPh3 → 2 (cymene)RuCl2(PPh3)

Such monomers adopt pseudo-octahedral piano-stool structures.

Precursor to catalysts

Treatment of [(cymene)RuCl2]2 with the chelating ligand TsDPENH gives (cymene)Ru(TsDPEN-H), a catalyst for asymmetric transfer hydrogenation.[2]

[(cymene)RuCl2]2 is also used to prepare catalysts (by monomerization with dppf) used in borrowing hydrogen catalysis,[3] a catalytic reaction that is based on the activation of alcohols towards nucleophilic attack.

It can also used to prepare other ruthenium—arene complexes.[4]

References
  1. Bennett, M. A.; Huang, T. N.; Matheson, T. W.; Smith, A. K. (1982). "16. (η6 -Hexamethylbenzene)Ruthenium Complexes". (η6-Hexamethylbenzene)ruthenium Complexes. Inorganic Syntheses. Vol. 21. pp. 74–78. doi:10.1002/9780470132524.ch16. ISBN 9780470132524.
  2. Takao Ikariya; Shohei Hashiguchi; Kunihiko Murata; Ryōji Noyori (2005). "Preparation of Optically Active (R,R)-Hydrobenzoin from Benzoin or Benzil". Organic Syntheses: 10.
  3. Hamid et al.; Advanced Synthesis & Catalysis Volume 349, Issue 10, pages 1555–1575, July 2, 2007; doi:10.1002/adsc.200600638
  4. Lautens, M., ed. (2001). Category 1, Organometallics: Compounds with Transition Metal—Carbon π-Bonds and Compounds of Groups 10–8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os). Stuttgart: Georg Thieme Verlag. doi:10.1055/sos-sd-001-00899. ISBN 978-3-13-112131-8.
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