1,3-Dehydroadamantane (original) (raw)
From Wikipedia, the free encyclopedia
1,3-Dehydroadamantane
 |
|
|---|---|
| Names | |
| Preferred IUPAC name Tetracyclo[3.3.1.13,7.01,3]decane | |
| Identifiers | |
| CAS Number | 24569-89-9 |
| 3D model (JSmol) | Interactive image |
| ChemSpider | 124482 |
| PubChem CID | 141122 |
| CompTox Dashboard (EPA) | DTXSID40179305  |
| InChI InChI=1S/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2Key: YNLPLYJBYLQXCY-UHFFFAOYSA-NInChI=1/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2Key: YNLPLYJBYLQXCY-UHFFFAOYAN | |
| SMILES C1C2CC34CC1CC3(C2)C4 | |
| Properties | |
| Chemical formula | 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). Infobox references |
Chemical compound
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.
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
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.
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]
- ^ 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.