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 chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
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 originally ...
of the compound thio
acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...
(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 Flash vacuum pyrolysis (FVP) is a technique in organic synthesis. It entails heating a precursor molecule intensely and briefly. Two key parameters are the temperature and duration (or residence time), which are adjusted to optimize yield, conver ...
of 2-mercapto
benzyl alcohol
Benzyl alcohol 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 alcohol is a colorless liquid w ...
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
sulfene
Sulfene is an extremely reactive chemical compound with the formula H2C=SO2. It is the simplest member of the sulfenes, the group of compounds which are ''S'',''S''-dioxides of thioaldehydes and thioketones, and have the general formula R2C=SO2.
...
s and ynamines.
See also
*
Dithiete
Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of ...
- analogue with two sulfur atoms
References
{{Reflist
Sulfur heterocycles
Four-membered rings