Oxidative Properties of Triflic Anhydride. Oxidation of Alcohols and Sulfides.
The reaction of dimethyl sulfide with triflic anhydride leads to the formation of the corresponding dimethyl(trifluoromethanesulfonyl)sulfonium salt. The latter can be used in the mild oxidation of primary and secondary alcohols including unsaturated and natural ones to the corresponding carbonyl compounds in 34-75% yield. The reaction of various sulfides with triflic anhydride was studied. It was found that the reactions give rise to the corresponding dialkyl(trifluoromethanesulfonyl)sulfonium salts. Succeeding treatment with water leads to the formation of sulfoxides in 25-73% yield. Formation of sulfones does not proceed.
Nenajdenko
Valentine G.
VG
Department of Chemistry, Moscow State University, Moscow 119899, Russia, A. N. Nesmeyanov Institute of Elementorganic Chemistry, Academy of Sciences, Moscow, Russia, and Institute of Physiologically Active Compounds, Academy of Sciences, Chernogolovka, Russia.
Vertelezkij
Pavel V.
PV
Koldobskij
Andrej B.
AB
Alabugin
Igor V.
IV
Balenkova
Elizabeth S.
ES