[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

Autor: Katarzyna Włodarczyk, Piotr Borowski, Marek Stankevič
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 88-105 (2020)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.11
Popis: β-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.
Databáze: Directory of Open Access Journals