94718-51-1Relevant articles and documents
Tin-Pummerer rearrangement in the synthesis of O,S-acetal derivatives
Hatlelid, Jostein,Benneche, Tore,Undheim, Kjell
, p. 1092 - 1095 (2007/10/03)
α-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of α-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction. Acta Chemica Scandinavica 1997.
Chemistry of O-Silylated Ketene Acetals: Preparation of α-Siloxy Phenyl Sulfides and Methyl 3-(Phenylthio)butyrates from Alkyl Phenyl Sulfoxides
Kita, Yasuyuki,Tamura, Osamu,Yasuda, Hitoshi,Itoh, Fumio,Tamura, Yasumitsu
, p. 4235 - 4241 (2007/10/02)
Treatment of alkyl phenyl sulfoxides (2a-h) with O-methyl-O-tert-butyldimethylsilyl ketene acetal (1a) in dry acetonitrile in the presence of a catalytic amount of zinc iodide caused a Pummerer-type rearrangement to give α-siloxy phenyl sulfides (3a-h) under mild conditions.On the oder hand, treatment of the sulfoxide (2d) with O-methyl-O-trimethylsilyl ketene acetals (1b,c) under similar conditions gave carbon-carbon bond-formed products, methyl 3-(phenylthio)-butyrates (8 and 9).Keywords - O-methyl-O-tert-butyldimethylsilyl ketene acetal; alkyl phenyl sulfoxide; Pummerer rearrangement; α-siloxy phenyl sulfide; O-methyl-O-trimethylsilyl ketene acetal; carbon-carbon bond forming reaction; methyl 3-(phenylthio)butyrate; α-siloxy sulfide reaction
