Thietane


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.

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.

Reactions

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