Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The Synthesis of Trifluoromethylated 1,2-Diphenylvinyl Sulfone and It's Synthetic Utilities

  • Published : 1998.12.20
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Abstract

The treatment of 1,1-bis(phenylthio)-2,2,3,3,3-pentafluoropropylbenzene (1) with 2 equiv. of phenyllithium in THF at -78 ℃ resulted in the formation of isomeric mixture (70: 30) of trifluoromethylated 1,2-diphenylvinyl sulfide 2 in 87% yield. The further oxidation of 2 with m-chloroperbenzoic acid in methylene chloride afforded isomeric mixture (70:30) of trifluoromethylated 1,2-diphenylvinyl sulfone 3 in 87% yield. When 3 was reacted with carbon nucleophiles such as methyllithium, n-butyllithium, phenyllithium and lithium octylide, the corresponding addition-elimination adducts 4, 5, 6 and 7 were obtained in moderate to good yields. The reaction of 3 with 4 equiv. of tributyltin hydride in benzene at reflux temperature provided isomeric mixture (90 : 10) of trifluoromethylated 1,2-diphenylvinyl stannane 8 in 41% yield. The reaction of 8 with methyllithium in the presence of trimethylsilyl chloride gave isomeric mixtures (90: 10) of trifluoromethylated 1,2-diphenylvinyl silane 9 in 88% yield. Finally, the treatment of 8 with Br2 and 12 resulted in the formation of isomeric mixtures (90: 10) of trifluoromethylated 1,2-diphenylvinyl bromide 10 and iodide 11 in 72% and 90% yields, respectively.

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References

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