1,4-Dioxane: Difference between revisions

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The oxygen atoms are weakly [[Lewis base|Lewis-basic]]. It forms adducts with a variety of Lewis acids. It is classified as a [[HSAB theory|hard base]] and its base parameters in the [[ECW model]] are E<sub>B</sub> =1.86 and C<sub>B</sub> = 1.29.
 
Dioxane produces [[coordination polymer]]s by linking metal centers.<ref>{{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> In this way, it is used to drive the [[Schlenk equilibrium]], allowing the synthesis of dialkyl magnesium compounds.<ref name=Ullmann /> [[Dimethylmagnesium]] is prepared in this manner:<ref>{{cite journal |title=The Preparation of Dialkylmagnesium Compounds from Grignard Reagents|last1=Cope |first1=Arthur C. |journal=Journal of the American Chemical Society |volume=57 |page=2238 |year=1935 |doi=10.1021/ja01314a059 |issue=11}}</ref><ref>{{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=The Journal of Organic Chemistry |volume=27 |page=596 |year=1962 |doi=10.1021/jo01049a060 |issue=2}}</ref>
:2 CH{{sub|3}}MgBr + (C{{sub|2}}H{{sub|4}}O){{sub|2}} → MgBr{{sub|2}}(C{{sub|2}}H{{sub|4}}O){{sub|2}} + (CH{{sub|3}}){{sub|2}}Mg
 
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=== Explosion hazard ===
Like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive [[peroxide]]s. [[Distillation]] of these mixtures is dangerous. Storage underover metallic sodium could limit the risk of explosion.
 
=== Environment ===