- Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media
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The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.
- Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
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experimental part
p. 2394 - 2409
(2009/12/03)
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- Remarkable effect of water on functionalization of the phenyl ring in methyl-substituted benzene derivatives with F-TEDA-BF4
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Various N-F reagents reacted with hexamethylbenzene (1) forming side chain substituted alkoxides or esters in protic solvents, Ritter type side chain functionalization was observed in acetonitrile in the presence of trifluoroacetic acid, while in aqueous
- Kralj, Petra,Zupan, Marko,Stavber, Stojan
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p. 3880 - 3888
(2007/10/03)
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- Efficient synthesis of 4-fluorocyclohexa-2,5-dienone derivatives using n-fluoro-1,4-diazoniabicyclo[2.2.2]octane salt analogues
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4-Fluorocyclohexa-2,5-dienone derivatives were obtained in high yield by reaction of para substituted phenols with 1-fluoro-4-chloromethyl-1,4- diazoniabicyclo[2.2.2]octane bis(tetra-fluoro-borate) (1a, Selectfluor(TM) F- TEDA-BF4) or its 4-hyd
- Stavber, Stojan,Jereb, Marjan,Zupan, Marko
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p. 1375 - 1378
(2007/10/03)
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