Alpha-Methylstyrene → Cyclohexanone, 2-methyl-5-(1-methylethyl)-

Participants

Reaction Steps

The yields of the hydrogenated products were determined by gas chromatography (GC). Hydrogenation of terminal alkenes such as 1-octene and α-methylstyrene proceeded readily within 24 hours at room temperature with excellent yields (see Table 1, entries 5-7). Internal alkenes trans-2-octene, cis-cyclooctene, and norbornylene were also hydrogenated at room temperature (see Table 1, entries 8-10). Hydrogenation of (R)-(+)-limonene occurred selectively at the terminal position; the internal tri-substituted C═C bond was not hydrogenated (see Table 1, entry 11). At room temperature, hydrogenation of (+)-dihydrocarvone occurred only at the C═C bond, affording 5-isopropyl-2-methylcyclohexanone in 99% yield (see Table 1, entry 12).

Provenance & Evidence