Bornane

• Camphane
• Bornylan
• 1,7,7 - trimethylbicyclo [2.2.1] heptan

" six-sided tablets " [ from alcohol ], "is characterized by volatility, and large Sublimationsvermögen from "

Fixed

156-157 ° C

161 ° C / 757 Torr

Template: Infobox chemical / molecular formula search available

As bornane the bicyclic hydrocarbon is known in organic chemistry, which forms the backbone of some terpenes. Important derivatives are the natural substances borneol and camphor. Because of the structural relationship to the latter, the hydrocarbon was also called camphane, but to the IUPAC nomenclature Rule A - 72 of this name (" Bornylan " as well ) are no longer used.

Nomenclature

The carbon atoms of Borna framework are subject to a special numbering: The methyl group at C -1 ( bridgehead ) of bicyclo [2.2.1 ] heptane skeleton bears the number 10, the " geminal " methyl groups at the " A Bridge " be with C -8 and C -9 numbered. The name camphane is misleading as an unsaturated hydrocarbon is called with a different structure camphene. So this should provide for the hydrogenation camphane, but this is not the case.

Production

Bornane obtained from bornyl by reduction ( dehalogenation ), including metallic sodium. Advantageously likely to be the reduction of camphor, was first reported by the discoverers of the Wolff -Kishner reduction. In this case, the hydrazone of the ketone was prepared at first, which was strongly heated with potassium hydroxide or sodium ethoxide. With the base is potassium tert- butoxide in dimethyl sulfoxide reduction could already be realized at room temperature.