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

• Main Authors: Katarzyna Włodarczyk, Piotr Borowski, Marek Stankevič
• Format: Article
• Language: English
• Published: Beilstein-Institut 2020-01-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: brønsted and lewis acids; dft; mechanistic studies; rearrangement; stereochemistry; sulfur atom migration
• Online Access: https://doi.org/10.3762/bjoc.16.11

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.