1,3-Cyclohexadiene → 5,6-Di(benzenesulfonyl)bicyclo[2.2.2]oct-2-ene

HRID 459601

Reaction equation

HRID 459601 reaction equation
[C:1]1([S:7](/[CH:10]=[CH:11]/[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]1[CH2:26][CH2:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:10]2[CH:11]([S:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:23]3[CH2:24][CH2:25][CH:26]2[CH:21]=[CH:22]3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 116051,3-CyclohexadieneHCID 5367099trans-1,2-Bis(phenylsulfonyl)ethylene

Product 1

HCID 127784115,6-Di(benzenesulfonyl)bicyclo[2.2.2]oct-2-eneYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

29.33 g of trans-1,2-diphenylsulfonylethylene was dissolved in 200 ml of toluene, and then, 11.4 ml of 1,3-cyclohexadiene was added, followed by dry distillation for 21 hours and then by recrystallization to obtain 35.66 g (yield: 96.5%) of 5,6-diphenylsulfonyl-bicyclo-[2,2,2]oct-2-ene.

Workup

  1. customby dry
  2. distillationdistillation for 21 hours
  3. customby recrystallization

Sources & evidence

ORD record
ord-a06b7c538b6d48bcb165f87e5c36eb9b
Source dataset
uspto-grants-2007_03
Patent number
US07193237B2

Linked notes

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