- Tin-Pummerer rearrangement in the synthesis of O,S-acetal derivatives
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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.
- Hatlelid, Jostein,Benneche, Tore,Undheim, Kjell
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p. 1092 - 1095
(2007/10/03)
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- Neighbouring Group Effects in a Pummerer-Type Rearrangement: A Facile Entry into 3,1-Benzoxathiins
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Arylmethyl sulphoxides treated with trialkylsilyl halide and base undergo a Pummerer-type rearrangement to give α-siloxy and α-chlorosulphides.However, the presence of an ortho hydroxymethyl group results in the exclusive and efficient formation of the α-chlorosulphides, presumably mediated via an intramolecular attack to yield an alkoxysulphonium salt.These 2-(hydroxymethyl)aryl chloromethylsulphides can then be converted into the corresponding 3,1-benzoxathiins via an intramolecular cyclisation.Preliminary investigation of the chemistry of these 3,1-benzoxathiins, reveals that in one case, a novel base induced ring contraction occurs to yield a benzothiophene.
- Kersey, Ian D.,Fishwick, Colin W. G.,Findlay, John B. C.,Ward, Peter
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p. 6819 - 6834
(2007/10/02)
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- Chemistry of O-Silylated Ketene Acetals: Preparation of α-Siloxy Phenyl Sulfides and Methyl 3-(Phenylthio)butyrates from Alkyl Phenyl Sulfoxides
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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
- Kita, Yasuyuki,Tamura, Osamu,Yasuda, Hitoshi,Itoh, Fumio,Tamura, Yasumitsu
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p. 4235 - 4241
(2007/10/02)
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- THE CHEMISTRY OF O-SILYLATED KETENE ACETAL; PUMMERER REARRANGEMENT OF SULFOXIDES INTO α-SILOXYSULFIDES
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Treatment of sulfoxides with ketene silyl acetal in anhydrous acetonitrile in the presence of catalytic amount of zinc iodide causes a Pummerer rearrangement to give α-siloxysulfides under extremely mild conditions.
- Kita, Y.,Yasuda, H.,Tamura, O.,Itoh, F.,Tamura, Y.
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p. 4681 - 4682
(2007/10/02)
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