Mild and Selective Oxygenation of Sulfides to Sulfoxides and Sulfones by Perfluoro-cis-2,3-dialkyloxaziridines
Sulfides are oxidized to sulfoxides by stoichiometric amounts of perfluoro-cis-2,3-dialkyloxaziridines 2.The reactions proceed at -40 deg C with nearly complete selectivity and very good yields.Sulfoxides are also oxidized easily by 2 under mild conditions to corresponding sulfones.The oxidation of some bioactive sulfides (promazine, albendazole, biotin, and others) is also reported.
DesMarteau, Darryl D.,Petrov, Viacheslav A.,Montanari, Vittorio,Pregnolato, Massimo,Resnati, Giuseppe
p. 2762 - 2765
(2007/10/02)
Synthesis of Aldehydes from Phenylthiotrimethylsilylmethane
Phenylthiotrimethylsilylmethyl-lithium (4) reacts with alkyl halides to give 1-phenylthio-1-trimethylsilylalkanes (5), which can also be prepared by the addition of alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (8), or from bis(phenylthio)acetals (11).The 1-phenylthio-1-trimethylsilylalkanes (5) can be converted into the corresponding aldehyde (15) by oxidation to the sulphoxide (13), thermal rearrangement, and hydrolysis of the resultant O-silyl thioacetal (14).
Ager, David J.
p. 1131 - 1136
(2007/10/02)
A NEW METHOD FOR CONVERTING ALKYL HALIDES TO HOMOLOGOUS ALDEHYDES
Phenylthiotrimethylsilylmethyl lithium can be alkylated and the product hydrolysed to the aldehydes by oxidation and rearrangement.
Ager, David J.,Cookson, Richard C.
p. 1677 - 1680
(2007/10/02)
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