1,3-Dehydroadamantane

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1,3-Dehydroadamantane, formally tetracyclo[3.3.1.13,7.01,3]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 abeing derived from [1.3.3]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 R. Pincock and E.Torupka,[1] by reduction of 1,3-dihaloadamantane, according to the scheme below:

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 di-hydroxide 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:

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[2]

See also

References

  1. ↑ Richard E. Pincock and Edward J. Torupka (1969), Tetracyclo[3.3.1.13,7.01,3]decane. Highly reactive 1,3-dehydro derivative of adamantane J. Am. Chem. Soc., volume 91 issue 16, pp. 4593–4593; doi:10.1021/ja01044a072
  2. ↑ Shin-ichi Matsuoka, Naoto Ogiwara, and Takashi Ishizone (2006), Formation of Alternating Copolymers via Spontaneous Copolymerization of 1,3-Dehydroadamantane with Electron-Deficient Vinyl Monomers. Communication, J. Am. Chem. Soc., volume 128 issue 27, pp. 8708–8709;doi:10.1021/ja062157i


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