1,3-Dehydroadamantane
1,3-Dehydroadamantane or tetracyclodecane is an organic compound with formula C10H14, which can be obtained from adamantane by removal of two hydrogen atoms to create an internal bond. It is a polycyclic hydrocarbon, and can be viewed also as being derived from propellane by addition of a methylene bridge between the two larger rings.
Like other small-ring propellanes, this compound is substantially strained and unstable.
Synthesis
1,3-Dehydroadamantane was obtained in 1969 by Richard Pincock and Edward Torupka, by reduction of 1,3-dibromoadamantane according to the scheme below:Reactions
Oxidation
On standing in solution, it reacts with oxygen from air, yielding a peroxide. The latter converts to a dihydroxide by reaction with lithium aluminium hydride.Polymerization
Like 1.1.1-Propellane|propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain:In this scheme, 1,3-dehydroadamantane is reacted with acrylonitrile in a radical polymerization initiated with lithium metal in tetrahydrofuran. The resulting alternating copolymer has a glass transition temperature of 217 °C