sulfoxidecontaining

Sulfoxide-containing refers to chemical compounds that bear at least one sulfoxide functional group, defined as a sulfur atom double-bonded to one oxygen and single-bonded to two carbon substituents (R-S(=O)-R′). The sulfur atom is in the +4 oxidation state. When the two carbon substituents differ, the sulfoxide sulfur can be a stereogenic center, often allowing isolation of enantiomeric sulfoxides because the barrier to inversion at sulfur is sufficiently high in many cases.

The sulfoxide group is highly polar and imparts distinctive solubility and reactivity to molecules. Dimethyl sulfoxide (DMSO) is the best-known sulfoxide and serves as a versatile solvent and reaction medium. The class also includes other sulfoxides, including cyclic variants and sulfoxide-containing natural products such as alliin, a sulfur-containing compound found in garlic that is a sulfoxide precursor to other sulfur compounds.

Synthesis and reactivity commonly involve oxidation of sulfides (thioethers) to sulfoxides. Oxidation with mild oxidants such as m-chloroperbenzoic acid (mCPBA), Oxone, or hydrogen peroxide under selective conditions can stop at the sulfoxide stage; harsher conditions may yield sulfones (R-S(=O)2-R′). Sulfoxides are used as solvents, intermediates in organic synthesis, and as chiral ligands or auxiliaries in asymmetric catalysis. They also appear in pharmaceuticals and materials science as functionalized building blocks.

Safety and handling depend on the specific compound. DMSO is relatively nonvolatile and low-odor but can carry dissolved substances through the skin, so appropriate handling and waste disposal practices apply.