Transformations of cyclohexene oxide were studied in a recirculation reactor and a flow system over silica-supported transition and early transition metal catalysts. Hydrogen pressure dependence of the transformations was measured over Cu/SiO2 at 403 K in the 0-98.7 kPa range. Deuterium distribution in the reactant and products were determined at 20 kPa D-2 pressure. The reactions were studied in the flow reactor under D-2 stream over Cu/SiO2 (373 K, 403 K, 443 K, 523 K), Pd/SiO2 (403 K), and Rh/SiO2 (403 K) catalysts too. Deuterium distributions were determined at the commonly used 403 K. Over each catalyst, in both reactor types three main transformation pathways were found. Single C-O scission occurred via isomerization and hydrogenation. Double C-O cleavage, that is, deoxygenation was also found to be important. Product distribution varied from catalyst to catalyst and it was influenced by the conditions, as well as the reactor types. Deuterium distribution revealed significant differences in the elementary surface processes over the catalysts. Detailed mechanistic interpretation of the transformations is offered.