Title
Regiospecific synthesis of <tex>$\alpha$</tex>-diones, <tex>$\alpha$</tex>,<tex>$\alpha$</tex>-dialkoxyketones and <tex>$\alpha$</tex>-alkoxy-<tex>$\alpha$</tex>-sulfenylated ketones Regiospecific synthesis of <tex>$\alpha$</tex>-diones, <tex>$\alpha$</tex>,<tex>$\alpha$</tex>-dialkoxyketones and <tex>$\alpha$</tex>-alkoxy-<tex>$\alpha$</tex>-sulfenylated ketones
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Oxford ,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
56(2000) :35 , p. 6541-6548
ISSN
0040-4020
ISI
000088927300021
Carrier
E
Target language
English (eng)
Abstract
A convenient synthesis of alpha-diones and their monoprotected acetals, i.e. alpha-ketoacetals, was developed by mercury induced solvolysis of regiospecifically formed alpha-chloro-alpha-(alkylthio)ketones. Analogously, alpha-alkoxy-alpha-sulfenylated ketones were formed when reacting alpha-chloro-alpha sulfenylated ketones with an alkaline alcoholic medium. alpha-Alkoxy-alpha-sulfenylated ketones themselves could be transformed into alpha-diones or alpha-ketoacetals, which in turn were hydrolyzed under anhydrous conditions into the corresponding alpha-diones. (C) 2000 Elsevier Science Ltd. All rights reserved.
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