期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 125, 期 9, 页码 1339-1345出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2004.04.002
关键词
perfluoroalkanes; dibromotetrafluoroethane; catalysis; copper; carbonyl compounds; olefination
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. (C) 2004 Elsevier B.V. All rights reserved.
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