A REARRANGEMENT OF O,O-SILYLKETENE ACETALS LEADING TO GAMMA-THIOMETHYLATION OF BUTENOIC ACID-DERIVATIVES

Authors
JAROSKOVA L BOURGAUX M WENKIN I GHOSEZ L
Citation
L. Jaroskova et al., A REARRANGEMENT OF O,O-SILYLKETENE ACETALS LEADING TO GAMMA-THIOMETHYLATION OF BUTENOIC ACID-DERIVATIVES, Tetrahedron letters, 39(20), 1998, pp. 3157-3160
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
20
Year of publication
1998
Pages
3157 - 3160
Database
ISI
SICI code
0040-4039(1998)39:20<3157:AROOAL>2.0.ZU;2-Q
Abstract
Methylthiomethyl esters of alpha,beta-unsaturated acids 2 were convert ed into the corresponding ketene acetals 3 by O-silylation. Ketene ace tals rearranged in refluxing toluene to give, after methanolysis, the corresponding gamma-methylthiomethyl substituted methyl esters 4. In t he case of phenylthiomethylesters the products of alpha-substitution w ere observed. (C) 1998 Published by Elsevier Science Ltd. All rights r eserved.