Multiple pentafluorophenylation of 2,2,3,3,5,6,6-heptafluoro-3,6-dihydro-2H-1,4-oxazine with an organosilicon reagent : NMR and DFT structural analysis of oligo(perfluoroaryl) compounds
作者： Masakazu Nishida , Haruhiko Fukaya , Yoshio Hayakawa , Taizo Ono , Kotaro Fujii
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摘要: The reagent Me3Si(C6F5) was used for the preparation of a series perfluorinated, pentafluorophenyl-substituted 3,6-dihydro-2H-1,4-oxazines (2–8), which, otherwise, would be very difficult to synthesize. Multiple pentafluorophenylation occurred not only on heterocyclic ring starting compound 1 (Scheme), but also in para position introduced C6F5 substituent(s) leading compounds with one three nonafluorobiphenyl (C12F9) substituents. While tris(pentafluorophenyl)-substituted 3 could isolated as sole product by stoichiometric control reagent, higher-substituted 5–8 obtained mixtures. structures oligo(perfluoroaryl) were confirmed 19F- and 13C-NMR, MS, and/or X-ray crystallography. DFT simulations 13C-NMR chemical shifts performed at B3LYP-GIAO/6-31++G(d,p) level geometries optimized B3LYP/6-31G(d) level, technique that proved useful accomplish full NMR assignment these complex products.
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sci-hub.se 参考文章(30)
A. A. Goodwin, F. W. Mercer, M. T. McKenzie, Thermal behavior of fluorinated aromatic polyethers and poly(ether ketone)s Macromolecules. ,vol. 30, pp. 2767- 2774 ,(1997) , 10.1021/MA9606768
Yan Li, Philip Wai Hong Chan, Nian-Yong Zhu, Chi-Ming Che, Ruthenium(II) Porphyrin Catalyzed Imine Aziridination and Crystal Structures of (meso-Tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) Complexes Containing PhNCH(p-ClPh), CPh2, and Pyridine Ligands Organometallics. ,vol. 23, pp. 54- 66 ,(2004) , 10.1021/OM034128B
Masakazu Nishida, Haruhiko Fukaya, Taizo Ono, Synthesis and Conformational Studies of Methylated, Highly Branched Fluoroolefins: Gear‐Meshed Conformational Isomers European Journal of Organic Chemistry. ,vol. 2003, pp. 3648- 3658 ,(2003) , 10.1002/EJOC.200300287
Kin-ya Tomizaki, Andrey B Lysenko, Masahiko Taniguchi, Jonathan S Lindsey, Synthesis of phenylethyne-linked porphyrin dyads Tetrahedron. ,vol. 60, pp. 2011- 2023 ,(2004) , 10.1016/J.TET.2004.01.003
Masakazu Nishida, Ashwani Vij, Robert L. Kirchmeier, Jean'ne M. Shreeve, Synthesis of Polyfluoro Aromatic Ethers: A Facile Route Using Polyfluoroalkoxides Generated from Carbonyl and Trimethysilyl Compounds Inorganic Chemistry. ,vol. 34, pp. 6085- 6092 ,(1995) , 10.1021/IC00128A020
Toshinobu Korenaga, Yusuke Kawauchi, Takahiro Kosaki, Tadashi Ema, Takashi Sakai, Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent Bulletin of the Chemical Society of Japan. ,vol. 78, pp. 2175- 2179 ,(2005) , 10.1246/BCSJ.78.2175
Kenji Miyatake, Kenichi Oyaizu, Eishun Tsuchida, Allan S. Hay, Synthesis and properties of novel sulfonated arylene ether/fluorinated alkane copolymers Macromolecules. ,vol. 34, pp. 2065- 2071 ,(2001) , 10.1021/MA0019959
Geoffrey W. Coates, Alex R. Dunn, Lawrence M. Henling, Joseph W. Ziller, Emil B. Lobkovsky, Robert H. Grubbs, PHENYL-PERFLUOROPHENYL STACKING INTERACTIONS : TOPOCHEMICAL 2+2 PHOTODIMERIZATION AND PHOTOPOLYMERIZATION OF OLEFINIC COMPOUNDS Journal of the American Chemical Society. ,vol. 120, pp. 3641- 3649 ,(1998) , 10.1021/JA974072A
Masakazu Nishida, Haruhiko Fukaya, Takashi Abe, A new synthetic method for perfluorocycloimines Journal of Fluorine Chemistry. ,vol. 76, pp. 3- 5 ,(1996) , 10.1016/0022-1139(95)03334-3
Wieland Tyrra, Dieter Naumann, On the attempted synthesis of salts with the trimethyl[bis(pentafluorophenyl)]silicate ion, [Me3Si(C6F5)2]−—A polyphenyl problem Journal of Fluorine Chemistry. ,vol. 126, pp. 1303- 1306 ,(2005) , 10.1016/J.JFLUCHEM.2005.06.013