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Aggarwal, V. K.; Crimmin, M.; Riches, S., Science of Synthesis, (2008) 37, 347.
An alternative method for the generation of sulfonium methylides is by the fluoride ion induced desilylation of a suitably functionalized sulfonium salt {see also Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section 27.1.3.2.1.327.1.3.2.1.3)]}.[141] Diphenyl[(trimethylsilyl)methyl]sulfonium trifluoromethanesulfonate (47) may be desilylated by treatment with an excess of cesium fluoride in a polar aprotic solvent at room temperature to generate diphenylsulfonium methylide (Scheme 44).[142] One major advantage of this variation is that it allows the regioselective generation of ylides that are contra-thermodynamic to those expected by deprotonation.[143] Diphenyl[(trimethylsilyl)methyl]sulfonium trifluoromethanesulfonate (47) may, in turn, be synthesized by the alkylation of diphenyl sulfide with (trimethylsilyl)methyl trifluoromethanesulfonate.
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References
[141] | Meeeee, M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[142] | Meeee, M.; Meee, M.; Meee, M., Meeeeeeee, (8888), 888. |
[143] | Meeeeeee, M.; Meeeee, M.; Meee, M.; Meee, M.; Meee, M., Meee. Meee., (8888), 888. |
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- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.