1,3-Dioxane or ''m''-dioxane is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the molecular formula . It is a saturated six-membered
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 ...
with two oxygen atoms in place of carbon atoms at the 1- and 3- positions.
1,4-Dioxane, which is of greater commercial value, is an
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
. Both dioxanes are colorless liquids.
Preparation and derivatives
The parent 1,3-dioxane is prepared by the reaction 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 ...
and
1,3-propanediol in the presence of Brönsted or Lewis acid catalysts.
Substituted derivatives can be used as
protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis.
In man ...
s for
carbonyl compound
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ...
s. are prepared from the reaction between a ketone or an aldehyde with 1,3-diols.
They can also be produced by the
Prins reaction
The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on react ...
.
Related compounds
1,3-
Dioxolanes are five-membered rings with the formula .
See also
*
1,2-Dioxane
*
1,4-Dioxane
*
Dithiane
References
{{DEFAULTSORT:Dioxane, 1,3-
Dioxanes
Cyclic ethers