Thietane is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

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 ALARM (Air Launched Anti-Radiation Missile) is a British anti-radiation missile designed primarily to destroy enemy radars for the purpose of Suppression of Enemy Air Defenses (SEAD). It was used by the Royal Air Force, RAF and is still used by ...

pheromones A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavi ...

and predator scent analogues. Both the mouse and human

olfactory receptors Olfactory receptors (ORs), also known as odorant receptors, are chemoreceptors expressed in the cell membranes of olfactory receptor neurons and are responsible for the detection of odorants (for example, compounds that have an odor) which give ...

MOR244-3 and

OR2T11 Olfactory receptor 2T11 is a protein that in humans is encoded by the ''OR2T11'' gene. Olfactory receptors interact with odorant molecules in the nose, to initiate a neuronal response that triggers the perception of a smell. The olfactory recepto ...

, 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 Trimethylene carbonate, or 1,3-propylene carbonate, is a 6-membered cyclic carbonate ester. It is a colourless solid that upon heating or catalytic ring-opening converts to poly(trimethylene carbonate) (PTMC). Such polymers are called aliphatic p ...

and

potassium thiocyanate Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides. The compound has a low melting point relative to most other inorganic salts. Uses Ch ...

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

sodium sulfide Sodium sulfide is a chemical compound with the formula Na2 S, or more commonly its hydrate Na2S·9 H2O. Both the anhydrous and the hydrated salts are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red ...

. :

Reactions

Nucleophiles like

butyllithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

can open the ring in thietane. Thietane also reacts with bromine. : Thietan_Disulfid

References

{{Authority control Sulfur heterocycles Four-membered rings Foul-smelling chemicals