dialkyloxysulfurane

Dialkyloxysulfuranes are a type of hypervalent organosulfur compound, specifically classified as (\sigma)-sulfuranes. These compounds have the general formula R₂(R'O)₂S, where R represents alkyl groups and R' represents oxygen. Unlike some other hypervalent sulfur compounds, acyclic and cyclic dialkyloxysulfuranes are stable at room temperature and are useful reagents in organic synthesis.1

These compounds are characterized by sulfur atoms with an expanded valence shell, typically accommodating more than eight valence electrons. This expansion is possible because sulfur, being in the third period, can utilize its 3d orbitals for bonding, a capability not available to second-period elements like oxygen. While some theoretical models suggest bonding through polar structures, there is evidence that sulfur's 3d orbitals contribute to the bonding in these hypervalent compounds.23