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Triethyloxonium tetrafluoroborate
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Triethyloxonium tetrafluoroborate : ウィキペディア英語版
Triethyloxonium tetrafluoroborate

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Triethyloxonium tetrafluoroborate is the organic oxonium compound with the formula ()BF4. It is often called Meerwein's Reagent after its discoverer Hans Meerwein. Also well known and commercially available is the related trimethyloxonium tetrafluoroborate. The compounds are white solids that dissolve in polar organic solvents. They are strong alkylating agents. Aside from the BF4 salt, many related derivatives are available.〔Hartwig Perst, Dave G. Seapy "Triethyloxonium Tetrafluoroborate" in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, New York, 2008. . Article Online Posting Date: March 14, 2008〕
==Synthesis and reactivity==
Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether, and epichlorohydrin:
: 4 Et2O·BF3 + 2 Et2O + 3 C2H3(O)CH2Cl → 3 Et3O+BF4 + B()3
The trimethyloxonium salt is available from dimethyl ether via an analogous route. These salts do not have long shelf-lives at room temperature. They degrade by hydrolysis:
:()+BF4 + H2O → (CH3CH2)2O + CH3CH2OH + HBF4
The propensity of trialkyloxonium salts for alkyl-exchange can be advantageous. For example, trimethyloxonium tetrafluoroborate, which reacts sluggishly due to it low solubility in most compatible solvents may be converted in-situ to higher alkyl/more soluble oxoniums, thereby accelerating alkylation reactions.

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