1,3-Dehydroadamantane

1,3-Dehydroadamantane
Names
IUPAC name
Tetracyclo[3.3.1.13,7.01,3]decane
Identifiers
24569-89-9
ChemSpider 124482
Jmol-3D images Image
PubChem 141122
Properties
Molecular formula
C10H14
Molar mass 134.22 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 being 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-dibromoadamantane 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. 91 (16): 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". J. Am. Chem. Soc. 128 (27): 8708–8709. doi:10.1021/ja062157i.