Decalin

Decalin (decahydronaphthalene, also

known as bicyclo[4.4.0]decane and
sometimes decaline),[3] a bicyclic organic
compound, is an industrial solvent. A
colorless liquid with an aromatic odor, it is
used as a solvent for many resins or fuel
additives.[4]
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Infobox references

Isomers
Decalin occurs in cis and trans forms. The
trans form is energetically more stable
because of fewer steric interactions. cis-
Decalin is a chiral molecule without a
chiral center; it has a two-fold rotational
symmetry axis, but no reflective symmetry.
However, the chirality is canceled through
a chair-flipping process that turns the
molecule into its mirror image.
1: trans (left) and cis (right) isomers

2:
ball-and-stick model of cis-decalin
 3:
trans-decalin

4:
cis-decalin ring-flip

trans-Decalin

The only possible way to join the two six-

membered rings in the trans position
means the second ring needs to start from
two equatorial bonds (blue) of the first
ring. A six-membered ring does not offer
sufficient space to start out on an axial
position (upwards), and reach the axial
position of the neighboring carbon atom,
which then will be on the downwards side
of the molecule (see the model of
cyclohexane in figure 5). The structure is
conformationally frozen. It does not have
the ability to undergo a chair flip as in the
cis isomer. In biology this fixation is widely
used in the steroid skeleton to construct
molecules (such as figure 6) that play a
key role in the signalling between distantly
separated cells.
Reactions
Oxygenation of decalin gives the tertiary
hydroperoxide, which rearranges to
cyclodecenone, a precursor to sebacic
acid.[5]

Decalin is the saturated analog of

naphthalene and can be prepared from it
by hydrogenation in the presence of a
catalyst. This interconversion has been
considered in the context of hydrogen
storage.[6]
Occurrence
Decalin itself is rare in nature but several
decalin derivatives are known. They arise
via terpene-derived precursors or
polyketides.[7]

Safety
Decalin easily forms explosive[8]
hydroperoxides upon storage in the
presence of air.[9][10]