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{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 376724395
| Watchedfields = changed
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| ImageFile = Methylrhenium-trioxide-3D-balls.png
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| verifiedrevid = 431966651
| Name = methylrhenium trioxide
| ImageFile = Methylrhenium trioxide.png
| OtherNames = methyltrioxorhenium
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| ImageFile1 = Methylrhenium-trioxide-3D-balls.png
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| Section1 = {{Chembox Identifiers
| Name = Methylrhenium trioxide
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| CASNo = 70197-13-6
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| OtherNames = Methyltrioxorhenium(VII)
| IUPACName = Methyl(trioxo)rhenium(VII)
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| Section1 = {{Chembox Identifiers
| Abbreviations = MTO
| CASNo_Ref = {{cascite|correct|??}}
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| CASNo = 70197-13-6
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10621726
| PubChem = 2734010
| UNII = 883D8RDD5Q
| SMILES = C[Re](=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 = [http://fscimage.fishersci.com/msds/02075.htm External MSDS]
| ExternalSDS = [http://fscimage.fishersci.com/msds/02075.htm External MSDS]
| 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 [[organometallic compound]] 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 [[organometallic compound]] with the formula {{chem2|CH3\sReO3}}. It is a volatile, colourless solid that has been used as a [[catalyst]] in some laboratory experiments. In this compound, rhenium has a [[tetrahedral coordination geometry]] with one [[methyl]] and three oxo [[ligands]]. The [[oxidation state]] of [[rhenium]] 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 [[tetramethyltin]]:<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 = [[Angew. Chem. Int. Ed. Engl.]] | 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 [[rhenium heptoxide]] and [[tetramethyltin]]:<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 = [[Angew. Chem. Int. Ed. Engl.]] | 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 [[Lewis acid]]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 [[Lewis acid]]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 [[olefin metathesis]] at 25 °C.
Methylrhenium trioxide serves as a [[heterogeneous catalyst]] for a variety of transformations. Supported on [[alumina]]/[[silica]], it [[catalyzes]] [[olefin metathesis]] at 25&nbsp;°C.


In solution, MTO catalyses for the oxidations with [[hydrogen peroxide]]. Terminal alkynes yield the corresponding acid or ester, internal alkynes yield diketones, and [[alkene]]s give epoxides. MTO also catalyses the conversion of [[aldehyde]]s and [[diazoalkane]]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 [[hydrogen peroxide]]. Terminal [[alkyne]]s yield the corresponding [[carboxylic acid]] or [[ester]], internal alkynes yield [[diketones]], and [[alkene]]s give [[epoxides]]. Methylrhenium trioxide also catalyses the conversion of [[aldehyde]]s and [[diazoalkane]]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 [[amines]] to [[N-oxide|''N''-oxides]] with [[sodium percarbonate]].<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 = [[Synlett]]|year = 2006|pages = 2661-2663|doi = 10.1055/s-2006-951487}}</ref>


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


[[Category:Rhenium compounds]]
[[Category:Organorhenium compounds]]

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[[de:Methyltrioxorhenium]]
[[ja:メチルトリオキソレニウム(VII)]]
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