cis,cis-1,5-Cyclooctadiene → 5-Decene
Reaction equation
[CH:1]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.[CH2:9]=[CH:10]CCCC>CO.[Ru]>[CH3:9][CH2:10][CH2:1][CH2:8][CH:7]=[CH:6][CH2:5][CH2:4][CH2:3][CH3:2]Participants
5
Reagents, catalysts & solvents 2
Procedure
In contrast to the “classical” ruthenium metathesis catalysts mentioned above, which react only with highly-strained olefins, alkylidenes 6 and 7 of Example 6 also promote the ROMP of less-strained monomers such as 1,5-cyclooctadiene, and are active in the metathesis of acyclic olefins in protic solvents. For example, 6 will dimerize 1-hexene in methanol to give 5-decene in 20% yield (Equation 3). In these systems, separation of catalyst from product is facilitated through addition of water to the reaction mixture. Olefins collected from the resulting two-phase system contain very low levels of detectable ruthenium.
Sources & evidence
- ORD record
- ord-d6edd4e4512f4ab9bfc4929ba9a824cd
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486279B2
Reaction notes
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