Electrochemical reactions of fluoro-compounds. Part II. The preparation of substituted fluoro-aromatic derivatives
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 282-288
- https://doi.org/10.1039/j39710000282
Abstract
2,4,5,6-Tetraflucro-1,3-phenylenediamine has been prepared by the electrochemical reduction of 1-amino-3-iminoheptafluorocyclohex-1-ene at a mercury cathode. Similarly, by reduction of other amino-imino-fluorocyclohex-1-enes and aminoheptafluorocyclohexenones, 2-trifluoromethyl-4,5,6-trifluoro-1,3-phenylenediamine, 1-amino-2,4,5,6-tetrafluorophenol, and 1-isopropylamino-2,4,5,6-tetrafluorophenol were obtained. The reduction of 1-methylamino-3-methyliminoheptafluorocyclohex-1-ene was anomalous, and gave 2,5,6-trifluoro-4H-NN′-dimethyl-1,3-phenylenediamine. 1-Amino-3-imino-pentafluorocyclopent-1-ene gave 1,3-diamino-3H-pentafluorocyclopent-1-ene without loss of fluorine. The polarographic reduction of the cyclohexene derivatives and some mono substituted heptafluorocyclohexa-1,3 and 1,4-dienes has also been investigated, and changes in E½ discussed in terms of the Hammett σp function.Keywords
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