Reaction of CBrF2-CBrF2 with hydrazones of aromatic aldehydes: Novel efficient synthesis of fluorocontaining alkanes, alkenes and alkynes |
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Authors: | Valentine G Nenajdenko Georgy N Varseev Alexey V Shastin |
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Institution: | a Department of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russia b Institute of Problems of Chemical Physics, Chernogolovka, Moscow 142432, Russia |
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Abstract: | An olefination of hydrazones of aromatic aldehydes by CBrF2-CBrF2 under copper catalysis was investigated. In situ prepared aldehydes hydrazones were converted to (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by reaction with CBrF2-CBrF2 in the presence of CuCl. Subsequent elimination of HF by sodium hydroxide resulted in stereospecific formation of fluorocontaining alkenes. Elimination proceeds stereoselectively, only Z-isomers of alkenes are formed. Elimination of two molecules of HF from (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by treatment with potassium tert-butoxide leads to formation of (bromodifluoromethyl)alkynes. As a result a simple and efficient transformation of aromatic aldehydes to range of various fluorinated alkanes, alkenes and alkynes was elaborated. |
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Keywords: | Perfluoroalkanes Dibromotetrafluoroethane Catalysis Copper Carbonyl compounds Olefination |
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