Thietane

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.

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.

Synthesis
Thietane can be produced from the reaction of trimethylene carbonate and potassium thiocyanate, but the yield is low.


 * $$\mathrm{C_4H_6O_3 + \ KSCN \longrightarrow \ C_3H_6S + \ KOCN + \ CO_2}$$

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


 * $$\mathrm{Br-(CH_2)_3-Br + \ Na_2S \longrightarrow \ C_3H_6S + 2 \ NaBr}$$

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