Alpha-Methylstyrene → 2,2-Dimethylbutane

Participants

Reaction Steps

Complex 6 was also tested for the hydrogenation of several other substrates. Heating 1-octene with complex 6 (10 mol %) under 4 atm H2 (THF-d8 solvent, 80° C., 24 hours) produced n-octane (70%) and internal octene isomers (30%, arising from isomerization of the 1-octene) (Table 6, entry 2). Prolonging the reaction time to 48 hours resulted in a higher yield (76%) of n-octane. Internal octene isomers (24%) remained at the end of the reaction, indicating that the terminal 1-octene is hydrogenated more rapidly than its internal isomers. The more sterically hindered olefins 3,3-dimethyl-1-butene and α-methylstyrene were also hydrogenated under the same reaction conditions (4 atm H2, 80° C.), albeit somewhat more slowly, affording neohexane (97%) and isopropylbenzene (48%) after 48 hours (Table 6, entries 3 and 4).

Provenance & Evidence