Norbornane (also known as bicyclo[2.2.1]heptane) is an organic compound and a saturated hydrocarbon with chemical formula C7H12. It is a crystalline compound with a melting point of 88 °C.[citation needed] The carbon skeleton is derived from cyclohexane ring with a methylene bridge in the 1,4- position, and is a bridged bicyclic compound. The compound is a prototype of a class of strained bicyclic hydrocarbons.[1]
The compound was originally synthesized by reduction of norcamphor.[2]
The name norbornane is derived from bornane, which is 1,7,7-trimethylnorbornane, being a derivative of camphor (bornanone). The prefix nor– refers to the stripping of the methyl groups from the parent molecule bornane.
See also
- 2-Norbornyl cation
- Norbornene
- Norbornadiene
- endo-Norborneol
- exo-Norborneol
- Norcamphor, the ketone derivative of norbornane
References
- ^ Fort, Raymond C. Adamantane. Studies in Organic Chemistry. Vol. 5. New York, NY: Marcel Dekker. p. 123.
Whereas noradamantane certainly is strained relative to, say, adamantane, it is the most stable of the tricyclononanes, being the only one that does not contain a bicyclo[2.2.1]heptane.
- ^ Komppa, Gust.; Beckmann, Siegfried (1934). “Der Grundkörper der Camphergruppe, das Bicyclo-[1.2.2]-heptan, und die stereoisomeren Norborneole”. Naturwissenschaften. 22: 171. doi:10.1007/BF01496254.
External links
- Norbornane in 3D Archived 2011-05-14 at the Wayback Machine
- Datasheet at Sigma-Aldrich