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

HRID 909989

Reaktionsgleichung

Reaktionsgleichung von HRID 909989
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:7]1([S:13](/[CH:16]=[CH:17]/[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[C:7]1([S:13]([CH:16]2[CH:17]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:19])[CH:3]3[CH2:4][CH2:5][CH:6]2[CH:1]=[CH:2]3)(=[O:14])=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

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

Produkt 1

HCID 127784115,6-Di(benzenesulfonyl)bicyclo[2.2.2]oct-2-eneAusbeute 104,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixed solution of 3.16 g (39.5 mmol) of 1,3-cyclohexadiene, 10.5 g (34.1 mmol) of trans-1,2-bis(phenylsulfonyl)ethylene, and 200 ml of toluene was refluxed for 7 hours. After that, the 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).

Aufarbeitung

  1. temperatureAfter that, the solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. customto yield a reaction mixture
  4. customThe reaction crude product
  5. customwas recrystallized (chloroform/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0b84019da8b34f139662471616d4b5ec
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08021915B2

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