View source for Chemistry:Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428799124
| Name = CpRuCl(PPh<sub>3</sub>)<sub>2</sub>
| ImageFile1 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium.png
| ImageSize1 = 120px
| ImageFile2 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium-from-xtal-1992-3D-balls.png
| ImageSize2 = 220px
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 32993-05-8
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 34560989
| PubChem = 78076231
|  SMILES = c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc[cH-1]1.[Cl-].[Ru+2]
|  InChI = 1/2C18H15P.C5H5.ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-5-3-1;;/h2*1-15H;1-3H,4H2;1H;/q;;-1;;+2/p-1
|  InChIKey = WGQMSPWAXIDKEY-REWHXWOFAY
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/2C18H15P.C5H5.ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-5-3-1;;/h2*1-15H;1-3H,4H2;1H;/q;;-1;;+2/p-1
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WGQMSPWAXIDKEY-UHFFFAOYSA-M}}
|Section2={{Chembox Properties
| Formula = C<sub>41</sub>H<sub>35</sub>ClP<sub>2</sub>Ru
| MolarMass = 726.19 g/mol
| Appearance = Orange solid
| Solubility = Insoluble
| MeltingPtC = 135
| MeltingPt_notes =
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|315|319|332|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|403+233|405|501}}
  }}
}}

'''Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium''' is the organoruthenium half-sandwich compound with formula RuCl(PPh<sub>3</sub>)<sub>2</sub>(C<sub>5</sub>H<sub>5</sub>).  It as an air-stable orange crystalline solid that is used in a variety of organometallic synthetic and catalytic transformations.  The compound has idealized [[Reflection symmetry|C<sub>s</sub> symmetry]].  It is soluble in [[Chemistry:Chloroform|chloroform]], [[Chemistry:Dichloromethane|dichloromethane]], and [[Chemistry:Acetone|acetone]].

==Preparation==
Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium was first reported in 1969 when it was prepared by reacting dichlorotris(triphenylphosphine)ruthenium(II) with [[Chemistry:Cyclopentadiene|cyclopentadiene]].<ref>{{cite journal | vauthors = Gilbert JD, Wilkinson, G | title = New Complexes of Ruthenium(II) with Triphenylphosphine and other Ligands | journal = J. Chem. Soc. | doi = 10.1039/J19690001749 | year = 1969 | pages = 1749}}</ref>

:[[Chemistry:Dichlorotris(triphenylphosphine)ruthenium(II)|RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>3</sub>]] + C<sub>5</sub>H<sub>6</sub>  →   RuCl(PPh<sub>3</sub>)<sub>3</sub>(C<sub>5</sub>H<sub>5</sub>) + HCl

It is prepared by heating a mixture of [[Chemistry:Ruthenium(III) chloride|ruthenium(III) chloride]], [[Chemistry:Triphenylphosphine|triphenylphosphine]], and [[Chemistry:Cyclopentadiene|cyclopentadiene]] in ethanol.<ref>Bruce, M. I.; Hamiester, C., Swincer, A. G., Wallis, R. C. "Some  η<sup>5</sup>-Cyclopentadienylruthenium(II) Complexes Containing Triphenylphosphine"  Inorganic Syntheses 1982, volume 21, pp 78-82. {{doi|10.1002/9780470132524}}</ref>

==Reactions==
Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II)  undergoes a variety of reactions often by involving substitution of the chloride.  With [[Chemistry:Phenylacetylene|phenylacetylene]] it gives the phenyl vinylidene complex:
: (C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuCl + HC<sub>2</sub>Ph + NH<sub>4</sub>[PF<sub>6</sub>]  →  [Ru(C:CHPh)(PPh<sub>3</sub>)<sub>2</sub>(C<sub>5</sub>H<sub>5</sub>)][PF<sub>6</sub>] + NH<sub>4</sub>Cl

Displacement of one [[Chemistry:Triphenylphosphine|PPh<sub>3</sub>]] by [[Chemistry:Carbon monoxide|carbon monoxide]] affords a [[Biology:Chirality|chiral]] compound.<ref>{{cite journal | vauthors = Blackmore T, Bruce MI,((Stone, F. G. A.))| year = 1971 | title = Some New η-Cyclopentadienyltuthenium Complexes | journal = J. Chem. Soc. A | pages = 2376–2382 | doi = 10.1039/J19710002376}}</ref>

:(C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuCl  +  CO   →   (C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)(CO)RuCl  +  PPh<sub>3</sub>

The compound can also be converted into the [[Physics:Hydride|hydride]]:<ref>{{cite journal |author1=Wilczewski, T. |author2=Bochenska, M. |author3= Biernat, J. |name-list-style=amp | year = 1981 | title = Cyclobentadienyl-Ruthenium Complexes | journal = J. Organomet. Chem. | doi = 10.1016/S0022-328X(00)84619-7 | volume = 215 | pages = 87–96}}</ref>
:(C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuCl + [[Chemistry:Sodium methoxide|NaOMe]]   →   (C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuH + NaCl + CH<sub>2</sub>O

A related complex is [[Chemistry:Tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate|tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate]], which has three labile [[Chemistry:Acetonitrile|MeCN]] ligands.

==Applications==
Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) serves as a [[Chemistry:Catalyst|catalyst]] for a variety of specialized reactions.  For example, in the presence of [[Chemistry:Ammonium hexafluorophosphate|NH<sub>4</sub>PF<sub>6</sub>]] it catalyzes the isomerisation of allylic alcohols to the corresponding saturated carbonyls.<ref>Murahashi, Shun-Ichi. "Ruthenium in Organic Synthesis" (2006) Wiley-VCH: Weinheim. {{ISBN|978-3-527-30692-3}}</ref>

==References==
{{reflist}}

{{Ruthenium compounds}}
[[Category:Organoruthenium compounds]]
[[Category:Triphenylphosphine complexes]]
[[Category:Cyclopentadienyl complexes]]
[[Category:Chloro complexes]]
[[Category:Ruthenium(II) compounds]]

{{Sourceattribution|Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium}}