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Studies on sulfinatodehalogenation. XX. Sodium dithionite-initiated addition of per- and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products

Corresponding Author

Wei-Yuan Huang

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032Search for more papers by this author

Yuan Xie,

Yuan Xie

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

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Long LÜ,

Long LÜ

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

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Wei-Yuan Huang,

Corresponding Author

Wei-Yuan Huang

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032Search for more papers by this author

Yuan Xie,

Yuan Xie

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

Search for more papers by this author

Long LÜ,

Long LÜ

Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032

Search for more papers by this author

First published: March 1991

https://doi.org/10.1002/cjoc.19910090211

Citations: 18

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Abstract

Per- and polyfluoroalkyl iodides [R_FI, R_F=Cl(CF₂)₄, 1a; Cl(CF₂)₆, 1b; Cl(CF₂)₈, 1c; n-C₆F₁₃, 1d; n-C₈F₁₇, 1e] reacted with cyclic enol ethers such as 2,3-dihydrofuran (2) and 3,4-dihydro-2H-pyran (3) in aqueous acetonitrile in the presence of sodium dithionite and sodium bicarbonate at room temperature (10–15°C) to give the corresponding 2-(F-alkyl) hemiacetals in high yields. The adducts were oxidized with Ce(NH₄)₂(NO₃)₆ in acetonitrile or reduced with LiAlH₄ in ether to form the corresponding 2-(F-alkyl)lactones or diols respectively in good yields. In the presence of p-toluenesulfonic acid, the adducts were refluxed in benzene and CH₃CN to produce the corresponding 2,3-dihydro-4-(F-alkyl) furan and 3,4-dihydro-5-(F-alkyl)-2H-pyran. This is a new and effective method for preparing these useful organofluorine compounds.

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Volume9, Issue2

March 1991

Pages 167-173

Studies on sulfinatodehalogenation. XX. Sodium dithionite-initiated addition of per- and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products

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Studies on sulfinatodehalogenation. XX. Sodium dithionite-initiated addition of per- and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products

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