1,3-Dehydroadamantane

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|thumb|none|400px|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|thumb|none|400px|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

References

References

1. (1969). "Tetracyclo[3.3.1.1^3,7.0^1,3]decane. Highly reactive 1,3-dehydro derivative of adamantane". [[J. Am. Chem. Soc.]].
2. (2006). "Formation of Alternating Copolymers via Spontaneous Copolymerization of 1,3-Dehydroadamantane with Electron-Deficient Vinyl Monomers". J. Am. Chem. Soc..