Beilstein J. Org. Chem.2020,16, 88–105, doi:10.3762/bjoc.16.11
Marie Curie-Skłodowska Sq., 20-031 Lublin, Poland 10.3762/bjoc.16.11 Abstract 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 sulfuratommigration depends on the type of acid used for the
control experiments and DFT calculations.
Keywords: Brønsted and Lewis acids; DFT; mechanistic studies; rearrangement; stereochemistry; sulfuratommigration; Introduction
Among all organic reactions, rearrangements are an exciting class of transformations where unusual or even unexpected products can
, yielding the corresponding β/γ-mercaptoalkylphosphine oxides. In this rearrangement, a sulfur atom transfers from phosphorus to carbon, whereas the phosphorus–carbon bonds remain intact. Depending on the type of acid, sulfuratommigration may occur at the β- or the γ-carbon atom.
Results and Discussion
In
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Graphical Abstract
Scheme 1:
Arbusov, phospha-Fries, and phospha-Brook rearrangements.