[1,3]/[1,4]-Sulfur atom migration in ß-hydroxyalkylphosphine sulfides.
Beilstein J Org Chem
; 16: 88-105, 2020.
Article
em En
| MEDLINE
| ID: mdl-32082428
ABSTRACT
ß-Hydroxyalkylphosphine sulfides undergo [1,3]- or [1,4]-sulfur atom phosphorus-to-carbon migration in the presence of Lewis or Brønsted acids. The direction of sulfur atom migration depends on the type of acid used for the reaction. In the presence of a Brønsted acid, mainly [1,3]-rearrangement is observed, whereas a Lewis acid catalyzes the [1,4]-sulfur migration. To gain insight into the mechanism of these transformations, the stereochemistry of these rearrangements have been tested, along with the conduction of some control experiments and DFT calculations.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Ano de publicação:
2020
Tipo de documento:
Article