Acyl anion equivalents. Synthesis of ketones and α-(phenylthio)ketones from the adducts of bis(phenylthio)carbanions and carbonyl compounds
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1074-1088
- https://doi.org/10.1039/p19790001074
Abstract
Bis(phenylthio)carbanions react with aldehydes and ketones to give α-hydroxybis(phenylthio)acetals. The aldehyde adducts give simple ketones with trifluoroacetic acid and α-(phenylthio) ketones with toluene-p-sulphonic acid. The effect of these reagents on the ketone adducts is also discussed. The mechanisms and scope of all the reactions are described. The synthesis of α-(phenylthio)ketones is regiospecific and makes these compounds available as specific enol equivalents.Keywords
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