Perfluorooctylation of aromatic compounds with perfluoroazooctane upon 185 nm irradiation in a two-phase system
作者： Takako Nakamura , Yoshinori Koga
DOI: 10.1039/A707171J
关键词: Irradiation 、 Phase (matter) 、 Photodissociation 、 Light intensity 、 Absorption (electromagnetic radiation) 、 Quantum yield 、 Photochemistry 、 Chemistry 、 Perfluorohexane 、 Spectral line
摘要: An efficient method for the preparation of perfluorooctylated aromatic and heteroaromatic compounds has been developed using photolysis perfluoroazooctane (E)-1 upon 185 nm irradiation. The use a two-phase system made up perfluorohexane solution suitable compound proved this reaction. photolytic mechanism irradiation also investigated on basis quantum yield, light intensity dependence UV–VIS spectra. It is shown that photoisomerized by one photon absorption to (Z)-isomer, with subsequent extrusion nitrogen second absorption.
rsc.org
sci-hub.se 参考文章(15)
G. Kaupp, O. Sauerland, Preparative laser photochemistry of perfluoroazoethane Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 56, pp. 375- 380 ,(1991) , 10.1016/1010-6030(91)80038-J
Teruo Umemoto, Yoshihiko Gotoh, Perfluoroalkylations of carbanions with (perfluoroalkyl)-phenyliodonium triflates (FITS reagents). Bulletin of the Chemical Society of Japan. ,vol. 59, pp. 439- 445 ,(1986) , 10.1246/BCSJ.59.439
Waldemar Adam, Francois Mazenod, Yoshinori Nishizawa, Paul S. Engel, Sharon A. Baughman, Woo-Ki Chae, Douglas W. Horsey, Helmut Quast, Bernhard Seiferling, Reluctant azoalkanes: the photochemical behavior of acyclic, bridgehead-centered azoalkanes on 185- and 350-nm irradiation Journal of the American Chemical Society. ,vol. 105, pp. 6141- 6145 ,(1983) , 10.1021/JA00357A028
K.J.L. Paciorek, R.H. Kratzer, J.H. Nakahara, H.M. Atkins, Perfluoroalkylbenzenesulfonyl chlorides, perfluoroalkylnaphthalenesulfonyl chlorides, and their metal salts Journal of Fluorine Chemistry. ,vol. 53, pp. 355- 367 ,(1991) , 10.1016/S0022-1139(00)80959-8
Andrzej Maciejewski, The application of perfluoroalkanes as solvents in spectral, photophysical and photochemical studies Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 51, pp. 87- 131 ,(1990) , 10.1016/1010-6030(90)87046-E
Takamasa Fuchikami, Iwao Ojima, Direct perfluoroalkylation of functionalized benzenes with perfluoroalkyl halides and copper bronze Journal of Fluorine Chemistry. ,vol. 22, pp. 541- 556 ,(1983) , 10.1016/S0022-1139(00)81229-4
Waldemar Adam, Ottorino De Lucchi, The Synthesis of Unusual Organic Molecules from Azoalkanes. New analytical methods (33) Angewandte Chemie. ,vol. 19, pp. 762- 779 ,(1980) , 10.1002/ANIE.198007621
William R. Dolbier, Structure, Reactivity, and Chemistry of Fluoroalkyl Radicals. Chemical Reviews. ,vol. 96, pp. 1557- 1584 ,(1996) , 10.1021/CR941142C
I. T. Horvath, J. Rabai, Facile Catalyst Separation Without Water: Fluorous Biphase Hydroformylation of Olefins Science. ,vol. 266, pp. 72- 75 ,(1994) , 10.1126/SCIENCE.266.5182.72
Wolfgang A. Herrmann, Christian W. Kohlpaintner, Water‐Soluble Ligands, Metal Complexes, and Catalysts: Synergism of Homogeneous and Heterogeneous Catalysis Angewandte Chemie. ,vol. 32, pp. 1524- 1544 ,(1993) , 10.1002/ANIE.199315241