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Switching of sulfonylation selectivity by nature of solvent and temperature: the reaction of β-dicarbonyl compounds with sodium sulfinates under the action of iron-based oxidantsстатья
Информация о цитировании статьи получена из
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Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 14 августа 2019 г.
- Авторы: Mulina O.M., Pirgach D.A., Nikishin G.I., Terent’ev A.O.
- Журнал: European Journal of Organic Chemistry
- Том: 2019
- Номер: 26
- Год издания: 2019
- Издательство: John Wiley & Sons Ltd.
- Местоположение издательства: United Kingdom
- Первая страница: 4179
- Последняя страница: 4188
- DOI: 10.1002/ejoc.201900258
- Аннотация: Selectivity of sulfonylation of β-ketoesters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by a type of a solvent and reaction temperature. α-Sulfonyl β-ketoesters are obtained when the process is conducted in THF:H2O solution at 40 °C. The change of the solvent to i-PrOH:H2O and refluxing of a reaction mixture provides α-sulfonyl esters — the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
- Добавил в систему: Мулина Ольга Михайловна