Science of Synthesis

Fernández, I.; Khiar, N., Science of Synthesis, (2007) 31, 1023.

Sulfoxides are transformed into the corresponding (diethylamino)sulfonium salts by treatment with N-ethyl-N-sulfinylethanaminium tetrafluoroborate. In the case of chiral diaryl sulfoxides the reaction is accompanied by retention and/or racemization of the products; which operation occurs depends upon on the structure of the starting sulfoxide. For example, the asymmetry of phenyl 4-tolyl (R)-sulfoxide is destroyed by this treatment and both isomers of the tetrafluoroborate ‌67‌ are obtained (‌Scheme 41‌); however, when optically active dialkyl and alkyl aryl sulfoxides are the substrates, chirality may be retained in the products.[‌55‌]

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References

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• 8.Meeeee-Meee, (8888) M 88-8, 888.