29392-04-9

Upstream product

• 507-63-1 1-iodoheptadecafluorooctane 
• 123-31-9 hydroquinone 
• 114934-91-7 4-hydroxy-4-(perfluorooctyl)-2,5-cyclohexadien-1-one 
• 70775-39-2 dimethylsulfoxonium methylide 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 6814-64-8 methylenedimethyl sulfurane 

Downstream Products

• 144876-54-0 2-perfluorooctyl-1,4-benzoquinone 

Relevant academic research and scientific papers

Perfluoroalkyl migration in the rearrangement of 4-perfluoroalkyl-4-quinols

Heating a DMSO solution of 4-(perfluoro-n-alkyl)-4-hydroxy-2,5-cyclohexadien-1-one (4-perfluoroalkyl-4-quinols) in the presence of a catalytic amount of base brought about 1,2-migration of the perfluoroalkyl group to give 2-(perfluoro-n-alkyl)hydroquinone

1,2-Migration of Perfluoroalkyl Groups in Anionotropic Rearrangement. The Acyloin Rearrangement of 4-Perfluoroalkyl-4-quinols

Treatment of 4-perfluoroalkyl-4-quinols with a catalytic amount of potassium t-butoxide gave 2-(perfluoroalkyl)hydroquinones or 5-perfluoroalkyl-2-cyclohexene-1,4-diones in good to moderate yields depending upon the substitution pattern of the quinols.Similarly, 2-hydroxy-3-methyl-2-perfluorooctyl-1-propyl-3-pyrrolin-5-one underwent the base-induced rearrangement to afford a perfluoroalkylated succinimide derivative.

DIRECT PERFLUOROALKYLATION OF FUNCTIONALIZED BENZENES WITH PERFLUOROALKYL HALIDES AND COPPER BRONZE

Perfluoroalkyl halides were found to react with functionalized benzenes in the presence of copper bronze to give the corresponding perfluoroalkylated products directly in moderate to good yields.The reaction may involve' active species' other than perfluoroalkylcopper species.Synthetic utility and possible mechanisms of the present one-step reaction are discussed.