The Chemistry of Sulfonyl Fluorides: SF5 and/or SO2F Containing Compounds as Precursors to Sulfonic Acids

Author

Robin Joyce Terjeson, Portland State University

Sponsor

Portland State University. Environmental Sciences and Resources Ph. D. Program

First Advisor

Gary L. Gard

Date of Publication

1989

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.) in Environmental Sciences and Resources: Chemistry

Department

Environmental Science and Management

Language

English

Subjects

Fluorine compounds, Sulfonic acids

DOI

10.15760/etd.1240

Physical Description

3, xi, 172 leaves: ill. 28 cm.

Abstract

Sulfonyl fluoride systems and their derivatives, RS0₂F, where R represents hydrocarbon/fluorocarbon moieties continue to be of considerable interest. The incorporation of the sulfonyl fluoride group (S0₂F) into molecular systems can lead to compounds that are useful as ion-exchange resins, surface active agents, fuel cell electrolytes, and strong sulfonic acids/salts.

Interest in preparing SF₅ containing sulfonyl fluorides led to the synthesis of the ᵝ-sultone, SF₅CHCF₂0S0₂, and its rearranged product. Hydrolysis of the sultone gave SF₅CH₂S0₂F which led to the sulfonic acid and salt, SF₅CH₂S0₃H•H₂0 and (SF₅CH₂S0₃)2Ca. Esters of the sultone were prepared by reaction of the sultone with fluorinated alcohols in the presence of NaF to give SF₅CH(S0₂F)C(O)OR where R = CH₂CF₃ and CH(CF₃)₂.

Polymeric SF₅/S0₂F containing esters were prepared by reaction of allyl esters, RCX(S0₂F)C(O)OCH₂CH=CH₂, in ultraviolet light where R = CF₃ or SF₅ and X= H or F. Fluorinated silver carboxylate salts have been useful in preparing fluoroesters from alkyl iodides. Therefore, a new silver salt, FS0₂CF₂C(0)0Ag was prepared and characterized; its reaction with (CH₃)₃SiI, HOCH₂CH₂I and alkyl bromides and iodides are reported.

In addition, new SF₅ containing fluoropolymers were synthesized via reaction of fluorinated olefins with SF₅Br. Reactions of SF₅ containing olefins with CF₃0Cl, C1F and Cl₂ provide reagents that may be of potential use as precursors to sulfonyl fluoride containing systems.

All new compounds were characterized by their respective infrared, nmr and mass spectra.

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Comments

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Persistent Identifier

http://archives.pdx.edu/ds/psu/4298

Recommended Citation

Terjeson, Robin Joyce, "The Chemistry of Sulfonyl Fluorides: SF5 and/or SO2F Containing Compounds as Precursors to Sulfonic Acids" (1989). Dissertations and Theses. Paper 1241.
https://doi.org/10.15760/etd.1240