Selective synthesis of α-organylthio esters and α-organylthio ketones from ß-keto esters and sodium S-organyl sulfurothioates under basic conditions.
Beilstein J Org Chem
; 17: 234-244, 2021.
Article
em En
| MEDLINE
| ID: mdl-33564334
ABSTRACT
We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of ß-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto-enol tautomers was possible, revealing them as significant intermediates for the mechanism elucidation.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Brasil