Oxygen → 2-Cyclohexen-1-one

HRID 618985Notes

Reaction equation

HRID 618985 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[O:19]=O>C(#N)C>[C:1]1(=[O:19])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:1]1([OH:19])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 977OxygenHCID 6547AzobisisobutyronitrileHCID 8079Cyclohexene2×

Product 2

HCID 131982-Cyclohexen-1-OLYield 1%HCID 135942-Cyclohexen-1-oneYield 4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 25 milliliters of acetonitrile, were added 1.64 grams (20 millimoles) of cyclohexene, and azobisisobutyronitrile (5 mole percent). The resultant mixture was stirred in an oxygen atmosphere at a temperature of 90° C. for 4 hours. In analysis of the product in the reaction mixture with gas chromatography, cyclohexene was transformed into 2-cyclohexen-1-one (cyclohexene-based selectivity 12%, yield 4%) and 2-cyclohexen-1-ol (cyclohexene-based selectivity 3%, yield 1%) with a transformation rate of 34 percent.

Sources & evidence

ORD record
ord-649c20d7c97a4a1681038222a93455ec
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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