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episulfide : ウィキペディア英語版
episulfide

Episulfides are a class of organic compounds that contain a saturated heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes.
The parent episulfide is thiirane. Most preparations of episulfides utilize a two-step method, converting an olefin to an epoxide before its conversion to the episulfide using either thiocyanate or thiourea. Common uses of episulfides in both academic and industrial settings most often involve their use as monomers in polymerization reactions.
==Preparation==
A number of chemists in the early 1900s, including Staudinger and Pfenninger (1916), as well as Delepine (1920), were the first to prepare and report episulfides.〔Sander, M. Thiiranes. Chem. Rev. 1966, 66(3), 297-339. 〕 However, both of these accounts were isolated incidents on single substrates. It was not until 1934 that Dachlauer and Jackel devised the first general synthesis of episulfides from epoxides using alkali thiocyanates and thiourea, which is still one of the most common methods for preparing episulfides today.〔
:
While the above method represents the most common method of preparation, episulfides can also be prepared from cyclic carbonates, hydroxy mercaptans, hydroxyalkyl halides, dihaloalkanes, and halo mercaptans, as well as a number of other preoxidized starting materials.〔 In addition, a reaction analogous to epoxidation has been reported involving the metal-catalyzed reaction of sulfur with alkenes.〔Adam, W.; Bargon ,R. M.; Schenk, W. A. JACS 2003, 125, 3871-3876. 〕
:alkene + "S" → episulfide

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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