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1,3,5-Trithiane is the
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
(CHS). This heterocycle
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 ...
is the cyclic trimer of the otherwise unstable species thioformaldehyde
Thioformaldehyde is the organosulfur compound with the formula CH2S. It is the simplest thioaldehyde. This compound is not observed in the condensed state (solid or liquid) because it oligomerizes to 1,3,5-trithiane, which is a stable colorless ...
. It consists of a six-membered ring with alternating methylene bridge
In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, ...
s and thioether groups. It is prepared by treatment of formaldehyde
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
with hydrogen sulfide
Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is toxic, corrosive, and flammable. Trace amounts in ambient atmosphere have a characteristic foul odor of rotten eggs. Swedish chemist ...
.
Trithiane is a building block molecule in organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
, being a masked source of formaldehyde
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.
:(CHS) + RLi → (CHS)(CHLiS) + RH
:(CHS)(CHLiS) + RBr → (CHS)(CHRS) + LiBr
:(CHS)(CHRS) + HO → RCHO + ....
Trithiane is the dithioacetal of formaldehyde. Other dithioacetal
In organosulfur chemistry, thioacetals are the sulfur ('' thio-'') analogues of acetals (). There are two classes: the less-common monothioacetals, with the formula , and the dithioacetals, with the formula (symmetric dithioacetals) or (asy ...
s undergo similar reactions to the above.
It is also a precursor to other organosulfur
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
s. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride
In chemistry, a sulfonyl halide consists of a sulfonyl () group singly bonded to a halogen atom. They have the general formula , where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > ...
:
:(CHS) + 9 Cl + 6 HO → 3 ClCHSOCl + 12 HCl
left, 200px, Sample of sym-trithiane.
Trithianes
Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalent groups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipientthioketone
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure ...
s and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH2)n(SCHR)3-n.
The conformation of trithianes has been well investigated.
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References