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Thietane
Chemical compound From Wikipedia, the free encyclopedia
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Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2] Some derivatives are of interest as drugs.[3]
Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.[4][5] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.[6]
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Synthesis
Thietanes are the subject of many preparative studies.[7][8] They are traditionally produced in modest or poor yields from 1,3-difunctionalized alkanes.[9] One example is the reaction of trimethylene carbonate and potassium thiocyanate.[10]
- C4H6O3 + KSCN → C3H6S + KOCN + CO2
An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.[11]
- Br−(CH2)3−Br + Na2S → C3H6S + 2 NaBr
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Reactions
Nucleophiles like butyllithium can open the ring in thietane.[12] Thietane also reacts with bromine.[13]
References
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