Sulfoxideja

Sulfoxideja, or sulfoxides, are a class of organosulfur compounds that feature the sulfinyl group, R–S(=O)–R'. The sulfur atom is bonded to two carbon substituents and one doubly bonded oxygen, giving the sulfur oxidation state of +4. The S=O bond is highly polar, and many sulfoxides are strong hydrogen bond acceptors and polar solvents. Simple examples include dimethyl sulfoxide (DMSO) and diethyl sulfoxide.

Chirality is possible at sulfur when the two substituents differ; such sulfoxides can be enantiomeric and, in many cases, racemize slowly, enabling use as chiral ligands or auxiliaries.

Synthesis commonly proceeds by partial oxidation of sulfides (thioethers) with oxidants like hydrogen peroxide or peracids (e.g., m-CPBA). Careful control avoids overoxidation to sulfones (R–S(=O)2–R').

Reactions and applications: Sulfoxides participate in the Pummerer rearrangement and related transformations. Dimethyl sulfoxide is a widely used solvent and, in some oxidation protocols (e.g., Swern oxidation), plays a reagent role. Chiral sulfoxides serve as ligands and auxiliaries; the sulfoxide moiety appears in drugs such as esomeprazole.

Natural and industrial context: Dimethyl sulfide released by marine organisms can be oxidized to DMSO in the atmosphere. Sulfoxides are important in organic synthesis, pharmaceuticals, and materials science.