Bicyclo[2.2.2]oct-5-en-2-one → Bicyclo[4.2.0]oct-3-en-7-one

HRID 1649277Notes

Reaction equation

HRID 1649277 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][C:2]2=[O:9]>C1CCCCC1>[CH:5]12[C:2](=[O:9])[CH2:3][CH:4]1[CH2:7][CH:8]=[CH:1][CH2:6]2

Participants

3

Reactant 1

HCID 137507Bicyclo[2.2.2]oct-5-en-2-one

Product 1

HCID 10997022Bicyclo[4.2.0]oct-3-en-7-one

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A 4% solution of (+)-bicyclo[2.2.2]oct-5-en-2-one was dissolved in cyclohexane and irradiated in a Pyrex apparatus under argon with a 250 w. medium pressure mercury lamp. After 50 hours, the starting product had been reacted quantitatively. The solution was concentrated by evaporation and the residue subjected to chromatography on 100 g. of silica gel with toluene/1% diethyl ether. Pure (-)-bicyclo[4.2.0]oct-3-en-8-one was obtained.

Workup

  1. customirradiated in a Pyrex apparatus under argon with a 250 w
  2. customthe starting product had been reacted quantitatively
  3. concentrationThe solution was concentrated by evaporation

Sources & evidence

ORD record
ord-5aa99102eccf4134977f18ee9761dd37
Source dataset
uspto-grants-1983_11
Patent number
US04415756

Reaction notes

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