Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

Abstract

The review is aimed in summarizing the most important aspects of the chemistry of 1,2,4‐trithiolanes, which form a relevant class of cyclic polysulfides abundant in nature. Some of them were identified as components of Lenthinus edodes (shiitaki mushrooms) extracts as well as of Parkia speciosa (stink bean), which are well known in Asian cuisine. In addition, they determine the flavor of boiled beef and roasted chicken. Thermal decomposition of 1,2,4‐trithiolanes, either in solution or in the gas phase, results in [3+2]‐cycloelimination leading to the release of reactive thiocarbonyl S‐sulfides existing in equilibrium with sulfur‐rich, three‐membered dithiiranes. Both, 1,2,4‐trithiolanes and the products of their decomposition react with low‐valent platinum and iron compounds forming the corresponding sulfur‐metal complexes. For example, iron‐sulfur clusters formed in these reactions are of interest as structural models of [Fe,Fe]‐hydrogenase mimics.

Diferrocenyl Thioketone: Reactions with (Bisphosphane)Pt(0) Complexes—Electrochemical and Computational Studies

“…Reactions of 1,2,4-trithiolanes and their S -oxides with Pt(0) complexes leading to diverse platinathiiranes and dithiolato complexes of type 3 and 4 , respectively, are summarized in a recent review [19].…”

1,3,5-Trithianes and sulfur monochloride/sodium sulfide: an alternative route to 3,5-disubstituted 1,2,4-trithiolanes

“…Five membered systems, such as 1,2,4-trithiolanes, as well as six and seven membered derivatives, namely tetrathianes and trithiepanes, represent interesting compounds both for their organoleptic properties and for their use as precursors of other polysulfurated compounds. In particular, as has been very recently reported by Mloston and coworkers [19], trithiolanes and their oxides take part in a variety of organic and organometallic transformations. Furthermore, several trithiolanes are present in nature, and are responsible of the typical flavourings and fragrances of various foods and plants, such as garlic, onion, mushrooms, meat [20].…”

Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonylS-methanides as diradical processes: a computational study

“…Diaryl-substituted thiocarbonyl S -methanides 1 react in the absence of a dipolarophile, with no exception, via a head-to-head dimerization yielding sterically crowded 1,4-dithianes of type 5 [ 9 – 10 ]. The analogous head-to-head dimerization course was reported for the thiocarbonyl S -methanide derived from benzyl octafluorodithiopentanoate [ 11 ].…”