HCID 131735118, compound → 1,1-Diphenylethylene

HRID 929398Notes

Reaction equation

HRID 929398 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]SN1C(=O)C=CC1=O>C(#N)C>[C:4]1([C:3]([C:2]2[CH:1]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH2:3])[CH:5]=[CH:6][CH:7]=[CH:1][CH:2]=1

Participants

3

Reactant 1

HCID 131735118HCID 131735118, compound

Product 1

HCID 107401,1-DiphenylethyleneYield 2,000%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Methylene hexylsulfanylmaleimide (25 mg, 0.116 mmol) was dissolved in acetonitrile (21 mL) and 1,1-diphenylethyene (203 μL, 1.16 mmol) to provide a 0.005M solution. The resulting solution was degassed for 30 minutes and irradiated in pyrex glassware for 5 minutes with stirring. Solvent was removed in vacuo and purification by flash chromatography (gradient elution in petroleum ether to 30% ethyl acetate in petroleum ether) afforded (4RS,5RS,7RS) 2-aza-2-methylenecyclohexane-4-hexylsulfanyl-5-phenyl-bicyclo[3.2.0]heptan-1,3-dione and (4RS,5SR,7RS) 2-aza-2-methylenecyclohexane-4-hexylsulfanyl-5-phenyl-bicyclo[3.2.0]heptan-1,3-dione as a colourless oil (30 mg, 0.075 mmol) as a mix of diastereoisomers (10:1) in 64% yield.

Sources & evidence

ORD record
ord-1914bf2a98714059bf45ee5023599343
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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