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- W60031446 abstract "The discovery of trialkyloxonium salts with the general formula R3O+BF4 - is credited to Meerwein, [1] who also investigated much of their chemistry. [2] Today, many different oxonium salts are known. The most important cations are Me3O+ and Et3O+ whereas the most important anion is the tetrafluoroborate species followed by the more stable SbF6 -, SbCl6 - or PF6 - analogues. [1] [3a] [b] Trialkyloxonium salts are well known for their excellent alkylating properties, particularly when applied to the alklyation of relatively weakly nucleophilic functional groups. Oxonium salts have also been employed as quarternizing agents for a variety of heterocyclic amines. One of the most significant drawbacks of Meerwein salts can be their insolubility in certain organic slovents, in which case, the use of the more soluble MeSO2CF3 (magic methyl) can be employed. The electrophilicity of several alkylating reagents have been demonstrated to decrease in the order of Me2Cl+SbF6 - > (MeO)2CH+BF4 - > Me3O+X- > Et3O+X-> MeSO2CF3 > MeSO2F > (MeO)2SO2 > MeI. [4]" @default.
- W60031446 created "2016-06-24" @default.
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- W60031446 date "2004-01-01" @default.
- W60031446 modified "2023-10-03" @default.
- W60031446 title "R<sub>3</sub>O<sup>+</sup>BF<sub>4</sub> <sup>-</sup>: Meerwein’s Salt" @default.
- W60031446 doi "https://doi.org/10.1055/s-2003-44976" @default.
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