Alpha-Methylstyrene → 2,2-Dimethylbutane
Reaction equation
[CH2:1]=CCCCCCC.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11]>>[CH3:16][CH2:17][C:12]([CH3:1])([CH3:13])[CH3:10].[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:9]Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-ff3c722126e74698b37bd3f2544417c9
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434666B2
Reaction notes
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