Trithiolane

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. 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. Trithiolane itself contributes to the flavor of truffles. 3,5-Dimethyltrithiolane is a component of the intense odor of durian.

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

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