Fluorination of organic compounds with K{sub 2}NiF{sub 6} and R-NiF{sub 3}. Synthesis and characterization of the novel fluorinated cation: (CHF{sub 2}){sub 4}N{sup +}
- Lawrence Berkeley National Lab., CA (United States)
The Simons Process electrochemical fluorination of organic compounds is speculated to involve a higher nickel fluoride, NiF{sub x} (X>2), which is formed at the nickel anode. To investigate this possibility, K{sub 2}NiF{sub 6} and R-NiF{sub 3} have been used in aHF solution to fluorinated CH{sub 3}CN, CH{sub 3}COF, (CH{sub 3}){sub 2}CO, CH{sub 3}C(O)NH{sub 3}{sup +}PF{sub 6}{sup -}, N{sub 2}O, NH{sub 4}{sup +}AsF{sub 6}, and (CH{sub 3}){sub 4}N{sup +} AsF{sub 6}{sup -}. Organic compounds were reacted with solutions (K{sub 2}NiF{sub 6}) or suspensions (R-NiF{sub 3}) of oxidizer below -60 {degrees}C ({approximately}3 h) then slowly warmed to room temperature. The products were characterized by {sup 1}H, {sup 19}F, {sup 13}C, and {sup 14}N NMR. CH{sub 3}CN yielded primarily CF{sub 3}CN with R-NiF{sub 3} and CF{sub 3}CF{sub 2}NF{sub 2} with K{sub 2}NiF{sub 6}, along with small amounts of fluorocarbons. CH{sub 3}COF and (CH{sub 3}){sub 2}CO underwent cleavage, yielding small amounts of CF{sub 3}COF and (CF{sub 3}){sub 2}CO but with COF{sub 2} and fluorocarbons as the major products. CH{sub 3}C(O)NH{sub 3}{sup +} also underwent cleavage reactions. N{sub 2}O and NH{sub 4}{sup +} were unreactive with either oxidizer. (CH{sub 3}){sub 4}N{sup +} yielded the novel fluorinated cation, (CHF{sub 2}){sub 4}N{sup +} with K{sub 2}NiF{sub 6}.
- OSTI ID:
- 560030
- Report Number(s):
- CONF-970443-; TRN: 97:005895-0107
- Resource Relation:
- Conference: 213. national meeting of the American Chemical Society, San Francisco, CA (United States), 13-17 Apr 1997; Other Information: PBD: 1997; Related Information: Is Part Of 213th ACS national meeting; PB: 2904 p.
- Country of Publication:
- United States
- Language:
- English
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