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Revision as of 08:34, 1 June 2011 editLuckas-bot (talk | contribs)929,662 editsm r2.7.1) (robot Adding: ja:メチルトリオキソレニウム(VII)← Previous edit Latest revision as of 09:31, 2 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,111 edits added Category:Methyl complexes using HotCat 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 376724395
| Watchedfields = changed
| ImageFile = Methylrhenium-trioxide-3D-balls.png
| verifiedrevid = 431966651
| Name = methylrhenium trioxide
| ImageFile = Methylrhenium trioxide.png
| OtherNames = methyltrioxorhenium
| ImageFile1 = Methylrhenium-trioxide-3D-balls.png
| Section1 = {{Chembox Identifiers
| Name = Methylrhenium trioxide
| CASNo = 70197-13-6
| OtherNames = Methyltrioxorhenium(VII)
| IUPACName = Methyl(trioxo)rhenium(VII)
| Section1 = {{Chembox Identifiers
| Abbreviations = MTO
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 70197-13-6
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10621726
| PubChem = 2734010
| UNII = 883D8RDD5Q
| SMILES = C(=O)(=O)=O
| InChI = 1/CH3.3O.Re/h1H3;;;;/rCH3O3Re/c1-5(2,3)4/h1H3
| InChIKey = PQTLALPZRPFYIT-YHFCCQKIAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/CH3.3O.Re/h1H3;;;;
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PQTLALPZRPFYIT-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = CH<sub>3</sub>ReO<sub>3</sub> | Formula = {{chem2|CH3ReO3}}
| C=1|H=3|Re=1|O=3
| MolarMass = 249.24 g/mol
| Appearance = white powder | Appearance = white powder
| Density = | Density =
| Solubility = highly soluble in water | Solubility = highly soluble in water
| MeltingPt = 112 °C (385 K) | MeltingPtC = 112
| BoilingPt = | MeltingPt_notes =
| BoilingPt =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| GHSPictograms = {{GHS03}}{{GHS07}}
| RPhrases =
| GHSSignalWord = Warning
| SPhrases = S22, S23, S24/25
| HPhrases = {{H-phrases|272|315|319|335|413}}
| PPhrases = {{P-phrases|210|220|221|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|405|501}}
}} }}
}} }}
'''Methylrhenium trioxide''', also known as '''methyltrioxorhenium''', is an ] with the formula CH<sub>3</sub>ReO<sub>3</sub>. It is a volatile, colourless solid has been used as a catalyst in some laboratory experiments. In this compound, Re has a tetrahedral coordination environment with one methyl and three oxo ligands. The oxidation state of rhenium is +7. '''Methylrhenium trioxide''', also known as '''methyltrioxorhenium(VII)''', is an ] with the formula {{chem2|CH3\sReO3}}. It is a volatile, colourless solid that has been used as a ] in some laboratory experiments. In this compound, rhenium has a ] with one ] and three oxo ]. The ] of ] is +7.


==Synthesis== ==Synthesis==
Methylrhenium trioxide is commercially available. It can be prepared by many routes, a typical method is the reaction of Re<sub>2</sub>O<sub>7</sub> and ]:<ref>{{cite journal | author = Herrmann, W. A.; Kratzer R. M.; Fischer R. W. | title = Alkylrhenium Oxides from Perrhenates: A New, Economical Access to Organometallic Oxide Catalysts | journal = ] | year = 1997 | volume = 36 | issue = 23 | pages = 2652–2654 | doi = 10.1002/anie.199726521}}</ref> Methylrhenium trioxide is commercially available. It can be prepared by many routes, a typical method is the reaction of ] and ]:<ref>{{cite journal |author1=Herrmann, W. A. |author2=Kratzer R. M. |author3=Fischer R. W. | title = Alkylrhenium Oxides from Perrhenates: A New, Economical Access to Organometallic Oxide Catalysts | journal = ] | year = 1997 | volume = 36 | issue = 23 | pages = 2652–2654 | doi = 10.1002/anie.199726521}}</ref>
:{{chem2|Re2O7 + (CH3)4Sn → CH3ReO3 + (CH3)3Sn\sO\sReO3}}
:Re<sub>2</sub>O<sub>7</sub> + (CH<sub>3</sub>)<sub>4</sub>Sn → CH<sub>3</sub>ReO<sub>3</sub> + (CH<sub>3</sub>)<sub>3</sub>SnOReO<sub>3</sub>


Analogous alkyl and aryl derivatives are known. Compounds of the type RReO<sub>3</sub> are ]ic, forming both 1:1 and 1:2 adducts with halides and amines. Analogous alkyl and aryl derivatives are known. Compounds of the type {{chem2|R\sReO3}} are ]s, forming both 1:1 and 1:2 adducts with halides and amines.


==Uses== ==Uses==
Methylrhenium trioxide serves as a heterogeneous catalyst for a variety of transformations. Supported on Al<sub>2</sub>O<sub>3</sub>/SiO<sub>2</sub>, it catalyzes ] at 25 °C. Methylrhenium trioxide serves as a ] for a variety of transformations. Supported on ]/], it ] ] at 25&nbsp;°C.


In solution, MTO catalyses for the oxidations with ]. Terminal alkynes yield the corresponding acid or ester, internal alkynes yield diketones, and ]s give epoxides. MTO also catalyses the conversion of ]s and ]s into an alkene.<ref> Hudson, A. “Methyltrioxorhenium” Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons: New York, 2002.</ref> In solution, methylrhenium trioxide catalyses for the oxidations with ]. Terminal ]s yield the corresponding ] or ], internal alkynes yield ], and ]s give ]. Methylrhenium trioxide also catalyses the conversion of ]s and ]s into an alkene,<ref>{{Cite encyclopedia |title=Methyltrioxorhenium |encyclopedia=Encyclopedia of Reagents for Organic Synthesis |publisher=John Wiley & Sons, Ltd |url=https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rn00017.pub3 |last=Hudson |first=Andrew |date=2013-09-16 |language=en |doi=10.1002/047084289x.rn00017.pub3 |isbn=978-0-471-93623-7 |last2=Betz |first2=Daniel |last3=Kühn |first3=Fritz E. |last4=Jiménez-Alemán |first4=Guillermo H. |last5=Boland |first5=Wilhelm}}</ref> and the oxidation of ] to ] with ].<ref>{{cite journal|title = Rhenium-Catalyzed Highly Efficient Oxidations of Tertiary Nitrogen Compounds to ''N''-Oxides Using Sodium Percarbonate as Oxygen Source|first1 = Suman L.|last1 = Jain|first2 = Jomy K.|last2 = Joseph|first3 = Bir|last3 = Sain|journal = ]|year = 2006|pages = 2661-2663|doi = 10.1055/s-2006-951487}}</ref>


==References== ==References==
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{{Rhenium compounds}} {{Rhenium compounds}}


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