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

Code

J1-7336 (C) - included in ARIS records

Head

PhD Marko Andrej Zupan

Period

1/1/1996 - 6/30/2001

Science

Natural sciences and mathematics (7)
Other (2)

Reseacher status

Researcher (8)
Junior expert or technical associate (1)

Education

Doctor's degree (7)
Other (2)

Sex

Woman (4)
Man (5)

Status

Employed at RO and RRD (1)
No data on employment in RO (2)
Retired (6)

No. of publications

0 (1)
10–99 (2)
100–999 (6)

Projects / Programmes source: ARIS

source: ARIS

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

Evaluation of bibliographic research performance indicators according to ARIS methodology

Citations Citations for bibliographic records in COBIB.SI that are linked to records in citation databases

source: WoS

source: Scopus

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	351
2.	03439	PhD Peter Bukovec	Chemistry	Researcher	1996 - 2001	544
3.	03418	Jana Darinka Burger		Researcher	1996 - 2001	12
4.	14680	PhD Jernej Iskra	Chemistry	Researcher	1996 - 2001	398
5.	08027	PhD Antonija Lesar	Chemistry	Researcher	1996 - 2001	121
6.	17143	Zdenka Sakelšek		Researcher	1999 - 2001	0
7.	06058	PhD Stojan Stavber	Chemistry	Researcher	1999 - 2001	310
8.	12369	PhD Aleš Zupan	Physics	Researcher	1998 - 2001	25
9.	01317	PhD Marko Andrej Zupan	Chemistry	Head	1999 - 2001	459

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	23,072
2.	0106	Jožef Stefan Institute	Ljubljana	5051606000	90,664

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.