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Please login to access the full content or check if you have access via Method 1: Reactions of Sulfoxides with N-Ethyl-N-sulfinylethanaminium Tetrafluoroborate

DOI: 10.1055/sos-SD-031-00953

Fernández, I.; Khiar, N.Science of Synthesis, (2007311023.

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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