1,3-Dehydroadamantane

1,3-Dehydroadamantane or tetracyclo[3.3.1.1^3,7.0^1,3]decane 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 [3.3.1]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:

File:1,3-dehydroadamantane.png

Scheme 1: 1,3-dehydroadamantane synthesis

Reactions

Oxidation

On standing in solution, it reacts with oxygen from air (with a half-life of 6 hours), yielding a peroxide. The latter converts to a dihydroxide by reaction with lithium aluminium hydride.

Polymerization

Like [1.1.1]propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain:

File:DehydroadamantanePolymer.png

Scheme 2: Polymerization of 1,3-dehydroadamantane.

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

See also

• [1.1.1]Propellane
• [2.2.2]Propellane