Decalin

Decalin occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric effects. 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. Image:Cis-trans isomerism of decahydronaphthalene.svg| Image:cis-decalin double chair.png|2: Image:trans-decalin double chair.png|3: File:Cisdecalin conformations.png|4: ==Synthesis==

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. ==Occurrence==

Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides. ==Reactions==

Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges via hydroxycyclodecanone to , a precursor to sebacic acid. ==Safety==

Decalin easily forms explosive hydroperoxides upon storage in the presence of air. == See also ==