1,3-Dehydroadamantane

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1,3-Dehydroadamantane
1,3-Dehydroadamantane.svg
Names
IUPAC name
Tetracyclo[3.3.1.13,7.01,3]decane
Identifiers
3D model (JSmol)
ChemSpider
Properties
C10H14
Molar mass 134.22 g·mol−1
Except where otherwise noted, data are 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 [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[edit]

1,3-Dehydroadamantane was obtained in 1969 by Richard Pincock and Edward Torupka,[1] by reduction of 1,3-dibromoadamantane according to the scheme below:

'Scheme 1. 1,3-dehydroadamantane synthesis

Reactions[edit]

Oxidation[edit]

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[edit]

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:

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[2]

See also[edit]

References[edit]

  1. ^ Pincock, Richard E.; Torupka, Edward J. (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. ^ Matsuoka, Shin'ichi; Ogiwara, Naoto; Ishizone, Takashi (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. PMID 16819846.