1,3,5-Trithiane
Encyclopedia
1,3,5-Trithiane is the chemical compound
with the formula
(CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene
and thioether groups. It is prepared by treatment of formaldehyde
with hydrogen sulfide
.
Trithiane is a building block molecule in organic synthesis
, being a masked source of formaldehyde
. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.3 + RLi → (CH2S)2(CHLiS) + RH2(CHLiS) + R’Br → (CH2S)2(CHR’S) + LiBr2(CHR’S) + H2O → R’CHO + ….
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
It is also a precursor to other organosulfur reagent
s. For example, chlorination in the presence of water affords the chloromethylsulfonyl chloride:3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
(CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....
and thioether groups. It is prepared by treatment of formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
with hydrogen sulfide
Hydrogen sulfide
Hydrogen sulfide is the chemical compound with the formula . It is a colorless, very poisonous, flammable gas with the characteristic foul odor of expired eggs perceptible at concentrations as low as 0.00047 parts per million...
.
Trithiane is a building block molecule in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
, being a masked source of formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.3 + RLi → (CH2S)2(CHLiS) + RH2(CHLiS) + R’Br → (CH2S)2(CHR’S) + LiBr2(CHR’S) + H2O → R’CHO + ….
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
It is also a precursor to other organosulfur reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...
s. For example, chlorination in the presence of water affords the chloromethylsulfonyl chloride:3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl