Thiete 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 an
unsaturated four-membered ring with three carbon atoms and one sulfur atom. It is more commonly encountered not on its own, but in
anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.
Structure
Thiete is a
valence isomer
In organic chemistry, two molecules are valence isomers when they are constitutional isomers that can interconvert through pericyclic reactions.
Benzene
There are many valence isomers one can draw for the C6H6 formula benzene. Some were original ...
of the compound thio
acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...
(CH
2=CHCH=S) and undergoes ring opening to it at temperatures below 400°C. Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.
Derivatives
Benzothietes are thietes annulated to benzo group. Such species are prepared by
flash vacuum pyrolysis of 2-mercapto
benzyl alcohol
Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl a ...
s. They are precursors to other S-heterocycles.
Thiete 1,1-dioxides are
sulfone
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of ...
s, the parent being C
3H
4SO
2. They are more stable than the parent thietes.
[Thomas C. Sedergran and Donald C. Dittmer "Thiete 1,1-dioxide and Chlorothiete 1,1-dioxide" Org. Synth. 1984, vol. 62, 210.] Substituted thiete-1,1-dioxides can also be prepared by
+2cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...
of
sulfenes and ynamines.
See also
*
Dithiete - analogue with two sulfur atoms
References
{{Reflist
Sulfur heterocycles
Four-membered rings