1,3-Dehydroadamantane
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| Preferred IUPAC name
Tetracyclo[3.3.1.13,7.01,3]decane | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H14 | |
| Molar mass | 134.222 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Dehydroadamantane or 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]- ^ 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. doi:10.1021/ja01044a072.
- ^ 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.