Tiolany

Tiolany is a term used in some chemical literature to refer to thiolanes, a class of cyclic organosulfur compounds. The term is most common in languages such as Polish, where tiolany is the plural noun used for these five-membered sulfur-containing rings; in English, the corresponding term is thiolanes, with the unsubstituted member named thiolane.

Structure and scope: Tiolanes are saturated, five-member heterocycles in which one atom of the ring is sulfur and the remaining four are carbon. The unsubstituted core resembles cyclopentane with one sulfur in the ring. Substituted tiolanes have hydrogen atoms replaced by alkyl or aryl groups, giving mono-, di-, and poly-substituted members.

Synthesis and reactions: Tiolanes are prepared by various ring-closure routes, including intramolecular cyclizations of sulfide precursors and hydrogenation of heteroaromatic sulfur compounds. They undergo typical reactions of saturated heterocycles: ring-opening with strong nucleophiles, functionalization at carbon adjacent to sulfur, and oxidation to sulfoxides or sulfones in the presence of oxidants. The sulfur in the ring can influence reactivity and odor.

Applications and occurrence: Tiolanes are mainly of interest in organic synthesis and in the study of sulfur-containing heterocycles. They are not widely used as bulk industrial solvents, but substituted tiolanes serve as intermediates for pharmaceutical and fragrance-related compounds and as ligands in certain coordination chemistry systems.

Safety: Many tiolanes have noticeable sulfur odors and can be irritants or toxic in concentrated form. Appropriate ventilation and handling are advised.

See also: thiolane, thietane, thiophene, organosulfur chemistry.