hrcak mascot   Srce   HID

Izvorni znanstveni članak

The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes

Marko Zupan ; Laboratory for Organic and Bioorganic Chemistry, Department of Chemistry, and J. Stefan Institute, University of Ljubljana, Slovenia
Jernej Iskra ; Laboratory for Organic and Bioorganic Chemistry, Department of Chemistry, and J. Stefan Institute, University of Ljubljana, Slovenia
Stojan Stavber ; Laboratory for Organic and Bioorganic Chemistry, Department of Chemistry, and J. Stefan Institute, University of Ljubljana, Slovenia

Puni tekst: engleski, pdf (14 MB) str. 1437-1447 preuzimanja: 266* citiraj
APA 6th Edition
Zupan, M., Iskra, J. i Stavber, S. (1996). The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes. Croatica Chemica Acta, 69 (4), 1437-1447. Preuzeto s https://hrcak.srce.hr/135981
MLA 8th Edition
Zupan, Marko, et al. "The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes." Croatica Chemica Acta, vol. 69, br. 4, 1996, str. 1437-1447. https://hrcak.srce.hr/135981. Citirano 07.03.2021.
Chicago 17th Edition
Zupan, Marko, Jernej Iskra i Stojan Stavber. "The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes." Croatica Chemica Acta 69, br. 4 (1996): 1437-1447. https://hrcak.srce.hr/135981
Harvard
Zupan, M., Iskra, J., i Stavber, S. (1996). 'The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes', Croatica Chemica Acta, 69(4), str. 1437-1447. Preuzeto s: https://hrcak.srce.hr/135981 (Datum pristupa: 07.03.2021.)
Vancouver
Zupan M, Iskra J, Stavber S. The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes. Croatica Chemica Acta [Internet]. 1996 [pristupljeno 07.03.2021.];69(4):1437-1447. Dostupno na: https://hrcak.srce.hr/135981
IEEE
M. Zupan, J. Iskra i S. Stavber, "The Chemistry of Organo Halogenic Molecules. 155. The Role of Reagent Structure in Halogenation of 9-Substituted Phenanthrenes", Croatica Chemica Acta, vol.69, br. 4, str. 1437-1447, 1996. [Online]. Dostupno na: https://hrcak.srce.hr/135981. [Citirano: 07.03.2021.]

Sažetak
9-Substituted phenanthrenes were used as target molecules in investigations of the effect of the reagent structure and reaction conditions on halogenation with bromine (1), CsSO4F (2) and F-TEDA (1-chloromethyl-4-fluoro-1,4-diazoniabicycloe[2,2,2]octane bis(tetra- fluoroborate), (3). 9-Methoxyphenanthrene (4) was converted to 9- bromo-10-methoxyphenanthrene (6a) and 9-bromo-10-hydroxy- phenanthrene (7a), while the amount of dealkylation depended on the solvent and was more pronounced in methanol than in acetonitrile, but no adduct was observed. Addition reaction became a major process in fluorination with CsS04F (2) in methanol and 88% of 9-fluoro-10,10-dimethoxy-9,10-dihydrophenanthrene (8b) was formed, while dealkylation occurred in acetonitrile. The course of fluorination of 9-methoxyphenanthrene with F-TEDA (3) could be completely manipulated by the choice of solvent and 9,9-difluoro-
10-oxo-9,10-dihydrophenanthrene (9b) was formed in acetonitrile, 9-fluoro-10-methoxyphenanthrene (6b) in trifluoroacetic acid and 9-fluoro-10,10-dimethoxy-9,10-dihydrophenanthrene (8b) in methanol. Bromination of 9-hydroxyphenanthrene (5) in acetonitrile resulted only in the substitution process, while 9-fluoro-10-hydroxyphenanthrene (7b) formed in the reaction with CsSO4F and F-TEDA was more reactive than the starting hydroxy derivative and, using a 2 molar ratio of F-TEDA, only 9,9-difluoro-10-oxo- 9,10-dihydrophenanthrene (9b) was formed.

Hrčak ID: 135981

URI
https://hrcak.srce.hr/135981

Posjeta: 374 *