Octafluorocyclopentene

Used Chemicals

• Octafluorocyclopentene [O0292]
• Butyllithium (ca. 15% in Hexane, ca. 1.6mol/L) [B0396]
• Bromobenzene [B0439]
• THF

Procedure

A Solution of bromobenzene (488 mg, 3.1 mmol) in anhydrous THF (10 mL) under nitrogen was cooled to -78 °C. Then butyllithium (ca. 1.6mol/L in hexane, 1.9 mL, 3.1 mmol) was added dropwise and stirred at the same temperature for 30 min. To this, octafluorocyclopentene (300 mg, 1.4 mmol) was added and stirred at -78 °C for 1 h. The reaction mixture was quenched with water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, hexane) to give 1 as a white solid (414 mg, 89% yield).

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane, Rf = 0.45).

Analytical Data

1,2-Diphenyl-3,3,4,4,5,5-hexafluorocyclopentene (1)

¹H NMR (270 MHz, CDCl₃); δ 7.43-7.29 (m, 10H)

Lead Reference

• Reaction of octafluorocyclopentene with various carbon nucleophiles
• S. Yamada, T. Konno, T. Ishihara, H. Yamanaka. J. Fluor. Chem. 2005, 126, 125.

References

• Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(2-methylbenzo[b]thiophen-3-yl)perfluorocycloalkene derivatives
  • M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc., Chem. Commun. 1992, 206.
• Light-triggered molecular devices: photochemical switching of optical and electrochemical properties in molecular wire type diarylethene species
  • S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275.
• Diarylethenes for Memories and Switches (a review)
  • M. Irie, Chem. Rev. 2000, 100, 1685.
• Reaction of octafluorocyclopentene with various carbon nucleophiles
  • S. Yamada, T. Konno, T. Ishihara, H. Yamanaka, J. Fluorine Chem. 2005, 126, 125.
• Efficient synthesis and properties of isomeric photochromic diarylethenes having a pyrrole unit
  • S. Pu, G. Liu, L. Shen, J. Xu, Org. Lett. 2007, 9, 2139.