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Organic and Coordination Chemistry of 1,2,4‐Trithiolanes
Author(s) -
Mlostoń Grzegorz,
Romański Jarosław,
Weigand Wolfgang,
Heimgartner Heinz
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801708
Subject(s) - chemistry , sulfur , thermal decomposition , flavor , decomposition , hydrogen sulphide , coordination complex , organic chemistry , platinum , metal , catalysis , food science
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.