Bicyclo[2.2.1]heptane-2-methanol transformations oil oxide catalysts

Bicyclo[2.2.1]heptane-2-methanol was synthesized by hydrogenation of bicycl o[2.2.1]hept-5-ene-2-methanol in a flow system on fixed-bed oxide catalysts , and its transformations were studied. Dehydration and isomerization of bi cycloheptene structure with the double-bond migration were found to be the main transformation routes. Thus, 2-methylenebicyclo[2.2.1]heptane (norcamp hene), the product of dehydration, was obtained with 47.2 or 61.0% yield in the presence of gamma-Al2O3 or aluminosilicate, respectively. The majority of norcamphene was isomerized to give bi- and monocyclic unsaturated hydro carbons differing in position of the double bond.