A rearrangement of O,O-silylketene acetals leading to γ-thiomethylation of butenoic acid derivatives

Methylthiomethyl esters of α,β-unsaturated acids 2 were converted into the corresponding ketene acetals 3 by O-silylation. Ketene acetals rearranged in refluxing toluene to give, after methanolysis, the corresponding γ-methylthiomethyl substituted methyl esters 4. In the case of phenylthiomethyleste...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 20; pp. 3157 - 3160
Main Authors Jaroskova, Libuse, Bourgaux, Manuel, Wenkin, Isabelle, Ghosez, Leon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.05.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Methylthiomethyl esters of α,β-unsaturated acids 2 were converted into the corresponding ketene acetals 3 by O-silylation. Ketene acetals rearranged in refluxing toluene to give, after methanolysis, the corresponding γ-methylthiomethyl substituted methyl esters 4. In the case of phenylthiomethylesters the products of α-substitution were observed. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00508-5