Trithiolane

Trithiolane
structure of 1,2,3- and 1,2,4-trithiolane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 1,2,3: InChI=1S/C2H4S3/c1-2-4-5-3-1/h1-2H2
    Key: LTTGPXZEANXUSL-UHFFFAOYSA-N
  • 1,2,4: InChI=1S/C2H4S3/c1-3-2-5-4-1/h1-2H2
    Key: QHGFEUAAQKJXDI-UHFFFAOYSA-N
  • 1,2,3: C1CSSS1
  • 1,2,4: C1SCSS1
Properties
C2H4S3
Molar mass 124.23 g·mol−1
Related compounds
Related compounds
 Dithiolane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In the area of organosulfur chemistry, trithiolane refers to either of two families of heterocycles with the C2S3 rings:

  • 1,2,3-trithiolanes with a C-C bond

parent: 1,2,3-trithiolane (registry number 6669–39–2), colorless liquid, boiling point = 224 °C

  • 1,2,4-trithiolanes with only one S-S bond

parent: 1,2,4-trithiolane (registry number 289–16–7), colorless solid, melting point 74-75 °C

Occurrence

A 1,2,3-trithiolane arises from treating of norbornene with elemental sulfur.[1] The same reaction also gives the pentasulfide (pentathiepane).

1,2,4-Trithiolanes are volatile components of many foods, especially after cooking. The frying of chicken produces 3,5-dimethyl-, 3,5-diisobutyl-1,2,4-trithiolane, 3-methyl-5-butyl-, and 3-methyl-5-pentyl-1,2,4-trithiolanes.[2] Trithiolane itself contributes to the flavor of truffles.[3] 3,5-Dimethyltrithiolane is a component of the intense odor of durian.[4]

1,2,4-Trithiolanes can be made artificially from partial oxidation of a thiocarbonyl to the thiosulfine, and then dimerization.[5] In such cases the ring adduct is in quilibrium with the reagents, and so slowly decomposes back to thiocarbonyls and elemental sulfur.[5]: 945 

References

  1. ^ Bartlett, Paul D.; Ghosh, Tirthankar (1987). "Sulfuration of the norbornene double bond". The Journal of Organic Chemistry. 52 (22): 4937–4943. doi:10.1021/jo00231a020.
  2. ^ Jayasena, Dinesh D.; Ahn, Dong Uk; Nam, Ki Chang; Jo, Cheorun (2013). "Flavour Chemistry of Chicken Meat: A Review". Asian-Australasian Journal of Animal Sciences. 26 (5): 732–742. doi:10.5713/ajas.2012.12619. PMC 4093335. PMID 25049846.
  3. ^ Pelusio, Fabio; Nilsson, Torben; Montanarella, Luca; Tilio, Roberto; Larsen, Bo; Facchetti, Sergio; Madsen, Jorgen (1995). "Headspace Solid-Phase Microextraction Analysis of Volatile Organic Sulfur Compounds in Black and White Truffle Aroma". Journal of Agricultural and Food Chemistry. 43 (8): 2138–2143. Bibcode:1995JAFC...43.2138P. doi:10.1021/jf00056a034.
  4. ^ Lim, Soo Chin; Juhari, Nurul Hanisah; Ola, Lasekan; Pak Dek, Mohd. Sabri; Nik Hadzir, Noor Hadzuin (2025). "Extraction and Identification of Durian's Volatile: A Review". ACS Food Science & Technology. 5 (5): 1751–1766. Bibcode:2025AFST....5.1751L. doi:10.1021/acsfoodscitech.4c00925.
  5. ^ a b Rolf Huisgen; J. Rapp (1997). "1,3-Dipolar Cycloadditions. 98. The Chemistry of Thiocarbonyl S-Sulfides". Tetrahedron. 53 (3): 939–960. doi:10.1016/S0040-4020(96)01068-X.

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