The thermal isomerization of norcarane



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The thermal isomerization of NORCARANE has been investigated in the temperature range 400-500[degrees]. In this temperature range norcarane isomerizes to methylenecyclohexane, cycloheptene, 1-methylcyclohexene, and 3-methylcyclohexene. This study was undertaken in order to test the theory that, structural isomerization of cyclopropanes occurs by cleaving a carbon-carbon bond in the cyclopropane ring to give a di radical intermediate, followed by a [1,2] hydrogen shift. Methylenecyclohexane, cycloheptene, and 1-methylcyclohexane are expected primary products. It is the 3-methylcyclohexene which is a surprising product since, if it a primary product and was formed by an intramolecular reaction then this could not have occured by a [1,2] hydrogen shift following the diradical formation, but would occur through a [1,4] hydrogen shift. This thesis shows that 3-mthylcyclohexene is not a primary product in the isomerization of norcarane and is probably a result of a bimolecuclar reaction involving one molecule of norcarane. A stereospecifically deuterium labelled norcarane was also synthesized and pyrolyzed.