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Effects of the structure of reagents on the halogenation of organic molecules

Research activity

Code Science Field Subfield
1.04.04  Natural sciences and mathematics  Chemistry  Organic chemistry 

Code Science Field
P003  Natural sciences and mathematics  Chemistry 
P390  Natural sciences and mathematics  Organic chemistry 
Keywords
fluorination, N-F reagents, xenon difluoride, norbornene, aromatic molecules, phenols
Evaluation (rules)
source: COBISS
Researchers (9)
no. Code Name and surname Research area Role Period No. of publicationsNo. of publications
1.  03440  PhD Nataša Bukovec  Chemistry  Researcher  1996 - 2001 
2.  03439  PhD Peter Bukovec  Chemistry  Researcher  1996 - 2001 
3.  03418  Jana Darinka Burger    Researcher  1996 - 2001 
4.  14680  PhD Jernej Iskra  Chemistry  Researcher  1996 - 2001 
5.  08027  PhD Antonija Lesar  Chemistry  Researcher  1996 - 2001 
6.  17143  Zdenka Sakelšek    Researcher  1999 - 2001 
7.  06058  PhD Stojan Stavber  Chemistry  Researcher  1999 - 2001 
8.  12369  PhD Aleš Zupan  Physics  Researcher  1998 - 2001 
9.  01317  PhD Marko Andrej Zupan  Chemistry  Head  1999 - 2001 
Organisations (2)
no. Code Research organisation City Registration number No. of publicationsNo. of publications
1.  0103  University of Ljubljana, Faculty of Chemistry and Chemical Technology  Ljubljana  1626990  10 
2.  0106  Jožef Stefan Institute  Ljubljana  5051606000  18 
Abstract
Following very intensive research in the area of the halogenation of organic molecules especially stressing in selective fluorination under mild reaction conditions we sistematically studied reactions of modern fluorinating reagents: N-F reagents (derivates of N-fluoro-1,4-diazoniabicyclo(2.2.2)octane, N-fluoro pyridinium salts, N-fluoro sulfonimides), caesium fluoroxysulphate and xenon difluoride with selected model aromatic molecules (phenoles, aromatic ethers, alky aromatics) and bicyclo alkenes (norbornene). Room temperature xenon difluoride fluorination of fluorene resulted in two ring fluoro-substituted products: 2-fluoro- and 4-fluorofluorene in 2:1 relative ratio. Fluorination of debenzofuran gave three products 1-fluoro-, 2-fluoro-, and 3-fluorodibenzofuran in 1:1:2 relative ratio and ion radicals were postulated as reactive intermediates. The ortho regioselectivity of fluorine introduction into a substrates within the group of diphenyl substituted aromatic molecules increases in the series: biphenyl, diphenylmethane, diphenyl ether. (J.Org.Chem. 1998, 63, 878). In the reaction of norbornene in acetonitrile with N-F reagents (F-TEDA-BF4, NFTh, NFSi, FPD-T) the formation of 2-exo-acetamido-7-syn-fluoro and 2-exo-acetamido-7-anti-fluoronorbornane was observed and the reaction pathway including carbonium ions intermediates was postulated (Chem. Lett. 1998, 641). In the reactions of phenols and anisole derivatives with F-L reagents the competition between three reaction proccesses : orho fluorofunctionalisation, ipso substitution, and addition-elimination was observed their relative intensity beeing depended on the structure of the reagent and the substrate.
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