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{{chembox |
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{{chembox |
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| verifiedrevid = 417625501 |
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| verifiedrevid = 428799124 |
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| Name = CpRuCl(PPh<sub>3</sub>)<sub>2</sub> |
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| Name = CpRuCl(PPh<sub>3</sub>)<sub>2</sub> |
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| ImageFile1 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium.png |
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| ImageFile1 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium.png |
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| ImageSize1 = 120px |
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| ImageSize1 = 120px |
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| ImageFile2 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium-from-xtal-1992-3D-balls.png |
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| ImageFile2 = Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium-from-xtal-1992-3D-balls.png |
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| ImageSize2 = 220px |
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| ImageSize2 = 220px |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 32993-05-8 |
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| CASNo = 32993-05-8 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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}} |
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| ChemSpiderID = 34560989 |
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| Section2 = {{Chembox Properties |
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| PubChem = 78076231 |
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| Formula = C<sub>41</sub>H<sub>35</sub>ClP<sub>2</sub>Ru |
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| SMILES = c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc1.. |
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| MolarMass = 726.19 g/mol |
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| 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 |
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| Appearance = Orange solid |
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| InChIKey = WGQMSPWAXIDKEY-REWHXWOFAY |
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| Solubility = Insoluble |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| MeltingPt = 135°C (408 K) |
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| 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 |
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| RPhrases = R20/21/22; R36/37/38 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| SPhrases = S22; S26; S36/37/39 |
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| StdInChIKey = WGQMSPWAXIDKEY-UHFFFAOYSA-M}} |
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|Section2={{Chembox Properties |
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| Formula = C<sub>41</sub>H<sub>35</sub>ClP<sub>2</sub>Ru |
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| MolarMass = 726.19 g/mol |
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| Appearance = Orange solid |
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| Solubility = Insoluble |
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| MeltingPtC = 135 |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|312|315|319|332|335}} |
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| 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}} |
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'''Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium''' is the ] 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. |
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'''Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium''' is the ] ] with formula RuCl(PPh<sub>3</sub>)<sub>2</sub>(C<sub>5</sub>H<sub>5</sub>). It as an ] orange crystalline solid that is used in a variety of ] synthetic and catalytic transformations. The compound has idealized ]. It is soluble in ], ], and ]. |
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==Structure and Properties== |
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The compound has idealized C<sub>s</sub> symmetry. It is soluble in chloroform, dichloromethane, and acetone. |
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==Preparation== |
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==Preparation== |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium was first reported in 1969 when it was prepared by reacting dichlorotris(triphenylphosphine)ruthenium(II) with cyclopentadiene.<ref>{{cite journal | author = Gilbert, J.; Wilkinson, G. | title = New Complexes of Ruthenium(II) with Triphenylphosphine and other Ligands | journal = ] | | doi = 10.1039/J19690001749 | year = 1969 | pages = 1749}}</ref> |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium was first reported in 1969 when it was prepared by reacting dichlorotris(triphenylphosphine)ruthenium(II) with ].<ref>{{cite journal | vauthors = Gilbert JD, Wilkinson, G | title = New Complexes of Ruthenium(II) with Triphenylphosphine and other Ligands | journal = ] | doi = 10.1039/J19690001749 | year = 1969 | pages = 1749}}</ref> |
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: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 |
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:] + 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 |
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It is easily prepared from ], ], and ] in ethanol.<ref>Bruce, M., Hamiester, C., Swincer, A., Wallis, R., and Ittel, S. (1982). “Some -Cyclopentadienylruthenium(II) Complexes Containing Triphenylphosphine.” Inorganic Syntheses (1982). 78-82. DOI: 10.1002/9780470132524</ref> |
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It is prepared by heating a mixture of ], ], and ] 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> |
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==Reactions== |
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==Reactions== |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) undergoes a variety of substitution reactions often by involving substitution of the chloride. With phenylacetylene it gives the phenyl vinylidene complex. |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) undergoes a variety of reactions often by involving substitution of the chloride. With ] it gives the ] complex: |
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: (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> → + NH<sub>4</sub>Cl |
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: (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> → + NH<sub>4</sub>Cl |
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Displacement of PPh<sub>3</sub> by carbon monoxide affords a ] compound.<ref>{{cite journal | author = Blackmore, T., Bruce, M., and Stone, F. | year = 1971 | title = New Cyclopentadienyltuthenium Complexes | journal = ] | pages = 2376–2382 | doi = 10.1039/J19710002376}}</ref> |
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Displacement of one ] by ] affords a ] 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> |
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:(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> |
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:(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> |
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The compound can also be converted into the ].<ref>{{cite journal | author = Wilczewski, T., Bochenska, M., and Biernat, J. | year = 1981 | title = Cyclobentadienyl-Ruthenium Complexes | journal = ] | doi = 10.1016/S0022-328X(00)84619-7 | volume = 215 | pages = 87}}</ref> |
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The compound can also be converted into the ]:<ref>{{cite journal |author1=Wilczewski, T. |author2=Bochenska, M. |author3= Biernat, J. |name-list-style=amp | year = 1981 | title = Cyclobentadienyl-Ruthenium Complexes | journal = ] | doi = 10.1016/S0022-328X(00)84619-7 | volume = 215 | pages = 87–96}}</ref> |
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:(C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuCl + ] → (C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuH + NaCl + CH<sub>2</sub>O |
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A related complex is ], which has three ] ] ]. |
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:(C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuCl + NaOMe → (C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)<sub>2</sub>RuH + NaCl + CH<sub>2</sub>O |
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==Applications== |
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==Applications== |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) serves as a ] for a variety of reactions. For example, in the presence of NH<sub>4</sub>PF<sub>6</sub> it catalyzes the ] 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> |
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Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) serves as a ] for a variety of specialized reactions. For example, in the presence of ] it catalyzes the ] of ]s to the corresponding saturated ]s.<ref>Murahashi, Shun-Ichi. "Ruthenium in Organic Synthesis" (2006) Wiley-VCH: Weinheim. {{ISBN|978-3-527-30692-3}}</ref> |
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==References== |
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==References== |
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{{Ruthenium compounds}} |
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{{Ruthenium compounds}} |
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{{Cyclopentadienide complexes}} |
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