Thietane

 ( Sulfur Heterocycles ) 

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom. Some derivatives are of interest as drugs.

Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues. Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.

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Synthesis Thietanes are the subject of many preparative studies. They are traditionally produced in modest or poor yields from 1,3-difunctionalized alkanes. One example is the reaction of trimethylene carbonate and potassium thiocyanate.

An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.

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Reactions Nucleophiles like butyllithium can open the ring in thietane. Thietane also reacts with bromine.

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