197362-75-7Relevant academic research and scientific papers
The role of F-N reagent and reaction conditions on fluoro functionalisation of substituted phenols
Pravst, Igor,Iskra, Maja Pape?,Jereb, Marjan,Zupan, Marko,Stavber, Stojan
, p. 4474 - 4481 (2006)
The effect of steric interactions on the regioselectivity of fluorination of para alkyl substituted phenols was investigated and the strong effect of size of the alkyl substituent, the structure of the F-N reagent and the solvent on the site of fluorination was established. The course of reaction obeyed a second order rate equation, while the fluorination process required higher ΔH≠ activation than oxidation or oxidative demethylation. Solvent polarity variations had a small effect on the rate of functionalisation, while an excellent Hammett correlation with ρ+=-2.3 was determined.
Fluorination of 4-alkyl-substituted phenols and aromatic ethers with fluoroxy and N-F reagents: Cesium fluoroxysulfate and N-fluoro-1,4-diazonia- bicyclo[2.2.2]octane dication salts case Dedicated to Prof. Dr. Boris ?emva in honor to his great contribution to fluorine chemistry.
Pravst, Igor,Stavber, Stojan
, p. 276 - 282 (2014/01/06)
4-Alkyl-substituted phenols and aromatic ethers were comparatively fluorinated with electrophilic fluorinating reagents such as cesium fluoroxysulfate (CFS), Selectfluor F-TEDA-BF4, and Accufluor NFTh in MeCN or MeOH. Reactions resulted in the formation of three types of products: 2-fluoro-4-alkyl-substituted corresponding compounds (5) as a result of ortho fluorination process, 4-alkyl-4-fluoro-cyclohexa-2,5- dienone compounds (6), resulting after an addition-elimination process, and 4-fluorosubstituted corresponding compounds (7) derived from ipso attack and release of the 4-alkyl group. The distribution of products depends on the bulkiness of alkyl groups at both positions and reaction media. The reaction in methanol proved more selective toward the formation of 2-fluoro derivatives. Tyramin and l-tyrozine were transformed with NFTh reagent in methanol to their fluorophenyl-substituted derivatives in good yield.
4-AMINO-7,8-DIHYDROPYRIDO[4,3-d]PYRIMIDIN-5(6H)-ONE DERIVATIVES
-
Page/Page column 36, (2010/08/08)
The invention provides compounds of the general Formula (I) where R1, R2, and A are defined herein, as well as the preparation, compositions and uses thereof.
Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
experimental part, p. 2394 - 2409 (2009/12/03)
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.
