Reaktion #1279112

Reaktionsgleichung

Methylene chloride

2-allyl-4-(trifluoromethyl)-1-vinylbenzene

→

6-(Trifluoromethyl)-1H-indene

Lösungsmittel

pentane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting solution was refluxed overnight (18 h)
2. 2
   SonstigeThe solvent was evaporated
3. 3
   Sonstigeto give a dark oil, which
4. 4
   SonstigeAfter pentane was carefully removed
5. 5
   Sonstige57 g (82.8%) of pure product was collected as slight brown oil

Vorschrift

Methylene chloride (0.6 L) was added to a 1 L flask containing 2-allyl-4-(trifluoromethyl)-1-vinylbenzene (80.0 g, 0.377 mol). Bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Grubbs catalyst, 1st generation) (3.1 g, 0.0038 mol) was added to the solution and the resulting solution was refluxed overnight (18 h). The solvent was evaporated to give a dark oil, which was passed through a silica gel plug using pentane. After pentane was carefully removed, 57 g (82.8%) of pure product was collected as slight brown oil. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.72 (s, 1H), 7.55 (d, 1H), 7.48 (d, 1H), 6.93 (m, 1H), 6.74 (m, 1H), 3.46 (brs, 1H).

Quelle