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| verifiedrevid = 399013842 |
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| IUPACName = Dimethylmagnesium |
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| ImageFile = Me2Mg.png |
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| CASNo = 2999-74-8 |
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| UNII = 3CAY272DHS |
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| PubChem = 18141 |
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| Mg = 1 | C = 2 | H = 6 |
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| SMILES = CC |
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| StdInChI = 1S/2CH3.Mg/h2*1H3; |
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| C=2 | H=6 | Mg=1 |
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| Solubility = Reacts |
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| Density = 0.96 g/cm3}} |
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'''Dimethylmagnesium''' is an ]. Like other dialkylmagnesium compounds, it is prepared by adding at least one equivalent of ] to a solution of ]:<ref>{{cite journal | doi = 10.1021/ja01314a059 | year = 1935 | last1 = ] | first1 = Arthur C. | journal = ] | volume = 57 | pages = 2238}}</ref><ref>{{cite journal | doi = 10.1021/jo01049a060 | title = Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone | year = 1962 | last1 = Anteunis | first1 = M. | journal = ] | volume = 27 | pages = 596}}</ref> |
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'''Dimethylmagnesium''' is an ]. It is a white ] solid.<ref>{{cite journal | authorlink = Arthur C. Cope | last1 = Cope | first1 = A. C. | title = The Preparation of Dialkylmagnesium Compounds from Grignard Reagents | journal = J. Am. Chem. Soc. | year = 1935 | volume = 57 | issue = 11 | pages = 2238–2240 | doi = 10.1021/ja01314a059 }}</ref><ref> |
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:2 MeMgX + dioxane {{eqm}} Me<sub>2</sub>Mg + MgX<sub>2</sub>(dioxane) |
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{{cite journal | last1 = Anteunis | first1 = M. | title = Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone | journal = ] | year = 1962 | volume = 27 | issue = 2 | pages = 596–598 | doi = 10.1021/jo01049a060 }}</ref> Dimethylmagnesium is used in the synthesis of organometallic compounds. |
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==Preparation== |
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Dioxane is used to precipitate magnesium halide as the solvate, driving the ] to give the dialkylmagnesium compound. |
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Like other dialkylmagnesium compounds, dimethylmagnesium is prepared by adding ] to a solution of ]:<ref name=RAA/> |
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:2 CH<sub>3</sub>MgX + 2 dioxane {{eqm}} (CH<sub>3</sub>)<sub>2</sub>Mg + MgX<sub>2</sub>(μ-dioxane)<sub>2</sub>↓ |
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In such procedures, the dimethylmagnesium exists as the ether adduct, not the polymer.<ref name= Westerhausen/> |
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Addition of ] causes precipitation of solid MgX<sub>2</sub>(μ-dioxane)<sub>2</sub>, a ].<ref name= Westerhausen>{{cite journal |doi=10.1002/chem.201903120|title=Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium |year=2019 |last1=Fischer |first1=Reinald |last2=Görls |first2=Helmar |last3=Meisinger |first3=Philippe R. |last4=Suxdorf |first4=Regina |last5=Westerhausen |first5=Matthias |journal=Chemistry – A European Journal |volume=25 |issue=55 |pages=12830–12841 |pmid=31328293 |pmc=7027550 }}</ref> This precipitation drives the ] toward (CH<sub>3</sub>)<sub>2</sub>Mg. Related methods have been applied to other dialkylmagnesium compounds.<ref name=RAA>{{cite book | author = Richard A. Andersen, Geoffrey Wilkinson | chapter = Bis[(Trimethylsilyl)Methyl] Magnesium | title = Inorganic Syntheses | journal = ] | doi = 10.1002/9780470132500.ch61 | year = 1979 | volume = 19 | pages = 262–265 | isbn = 978-0-471-04542-7 }}</ref> |
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The structure of this compound has been determined via ] to contain magnesium atoms surrounded by bridging methyl groups in a tetrahedral arrangement.<ref>{{cite journal | doi = 10.1016/S0022-328X(00)82217-2 | title = Die kristallstruktur des dimethylmagnesiums | year = 1964 | last1 = Weiss | first1 = E | journal = ] | volume = 2 | pages = 314 }}</ref> |
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Dimethylmagnesium can also be prepared by combining ] and magnesium.<ref>{{citation|title=Houben-Weyl Methods of Organic Chemistry Vol. XIII/2a, 4th Edition Organometallic Compounds of Group II of the Periodic Table (except mercury)|publisher=Georg Thieme Verlag|page=215|isbn=978-3-13-180654-3|date= 2014|language=German|url={{Google books|cSqGAwAAQBAJ||page=215|plainurl=yes}} |
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}}</ref><ref name="Jane E. Macintyre">{{citation|surname1=Jane E. Macintyre|title=Dictionary of Organometallic Compounds|publisher=CRC Press|page=2273|isbn=978-0-412-43060-2|date= 1994|language=German|url={{Google books|3kYZDa6rBjYC||page=2273|plainurl=yes}}}}</ref> |
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==Properties== |
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The structure of this compound has been determined by ]. The material is a polymer with the same connectivity as ], featuring tetrahedral magnesium centres, each surrounded by bridging methyl groups. The Mg-C distances are 224 pm.<ref>{{cite journal | last1 = Weiss | first1 = E. | title = Die Kristallstruktur des Dimethylmagnesiums | journal = ] | year = 1964 | volume = 2 | issue = 4 | pages = 314–321 | doi = 10.1016/S0022-328X(00)82217-2 }}</ref> |
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==Related compounds== |
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The linear chain structure seen for dimethylmagnesium is also observed for diethylmagnesium and dimethylberyllium.<ref>{{cite journal | last1 = Snow | first1 = A.I.|last2 = Rundle| first2=R.E.|title = Structure of Dimethylberyllium |
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|journal=]|year=1951|volume=4| issue = 4|pages=348–52|doi=10.1107/S0365110X51001100| bibcode = 1951AcCry...4..348S|hdl=2027/mdp.39015095081207|hdl-access=free}}</ref> Di(tert-butyl)magnesium is however a dimer.<ref>{{cite journal |doi=10.1021/om030091j |title=Di- ''tert'' -butylmagnesium: Synthesis and Structure |date=2003 |last1=Starowieyski |first1=Kazimierz B. |last2=Lewinski |first2=Janusz |last3=Wozniak |first3=Robert |last4=Lipkowski |first4=Janusz |last5=Chrost |first5=Andrzej |journal=Organometallics |volume=22 |issue=12 |pages=2458–2463 }}</ref> |
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==References== |
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==References== |
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