Reaction #336828

Reaction equation

1,3-cyclohexadiene

trans-1,2-bis(phenylsulfonyl)ethylene

→

5,6-bis(phenylsulfonyl)-bicyclo[2,2,2]octa-2-ene

Yield 104.6%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThen, the mixed solution was cooled
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   Otherto yield a reaction mixture
4. 4
   OtherThe reaction crude product
5. 5
   Otherwas recrystallized (chloroform/hexane)

Procedure

A mixed solution of 3.16 g (39.5 mmol) of 1,3-cyclohexadiene, 10.5 g (34.05 mmol) of trans-1,2-bis(phenylsulfonyl)ethylene, and 200 ml of toluene was refluxed for 7 hours. Then, the mixed solution was cooled and concentrated under reduced pressure to yield a reaction mixture. The reaction crude product was recrystallized (chloroform/hexane) to yield 5,6-bis(phenylsulfonyl)-bicyclo[2,2,2]octa-2-ene (13.8 g, 35.6 mmol, 90% yield).

Source