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Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = NHBu, NEt2, and OMe) |
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| Authors: | Nadezhda M Troshkova Yurij V Gatilov Vitalij D Shteingarts |
| Institution: | a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentiev Avenue 9, 630090 Novosibirsk, Russian Federation b Institute of Biological Chemistry and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrentiev Avenue 8, 630090 Novosibirsk, Russian Federation c Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation |
| Abstract: | Aminodefluorination of 2-n-butylamino- and 2-diethylaminopentafluoro-1,4-naphthoquinone by alkylamines HNR1R2 (NR1R2 = NHEt, NHnBu and NEt2) occurs at the 6- or 8-position and further, accordingly, at the 8- or at one of the 5- and 6-sites. The isomer ratio changes significantly in favor of a β-replacement product with solvent variation in the sequence: toluene < 1,4-dioxane < DMSO. n-Butylaminodefluorination of 2-methoxypentafluoro-1,4-naphthoquinone gives mixtures of fluorine substitution products both on the benzene and quinone rings. |
| Keywords: | Hexafluoro-1 4-naphthoquinone 2-Alkylaminopentafluoro-1 4-naphthoquinone Aminodefluorination Nucleophilic substitution Regioselectivity |
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