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2005
Thio compounds
P 0440
Highly Chemoselective Oxidation of Dithioester Enethiolates to Sulfenates: Applito the Synthesis of Ketene Dithioacetal S-Oxides. — In the presence of the
04- 073 cation
oxaziridine OAZ enethiolates generated from dithioesters undergo highly chemoselective oxidation to vinyl sulfenates. Reaction of the latter with alkyl halides leads to
ketene dithioacetal S-oxides. This provides a simple and straightforward route to ketene
dithioacetal S-oxides, which are useful synthetic synthons. Both the (E) and (Z) isomers
can be formed mainly depending on the reaction temperature. In contrast, using oxaziridine OAB double oxidation takes place yielding a vinyl sulfone product such as (X)
after alkylation. — (SANDRINELLI, F.; FONTAINE, G.; PERRIO*, S.; BESLIN, P.;
J. Org. Chem. 69 (2004) 20, 6916-6919; Lab. Chim. Mol. Thio-Org., CNRS, Inst. Sci.
Matiere Rayonnem., Univ. Caen, F-14050 Caen, Fr.; Eng.) — Jannicke
2005
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