Unusual reactivity of trifluoromethyl groups in meso-tetrakis(trifluoromethyl)porphyrin
作者： Anikó Nemes , Egmont Mérész , István Jalsovszky , Dénes Szabó , Zsolt Böcskei
DOI: 10.1016/J.JFLUCHEM.2017.05.009
关键词:
摘要: Abstract Based on the unusual reactivity of trifluoromethyl groups in nitrogen containing heterocycles, we synthesized appropriate porphyrin mono-, di-, tri- or tetra-carboxylic ester derivatives by treatment precursor meso-tetrakis(trifluoromethyl)porphyrin with an excess sodium- potassium alkoxide respective alcohol. This method offers efficient route for synthesis lower symmetry meso-substituted porphyrins compared to usual preparations utilizing stepwise condensation reactions. The structure tetrakis(butyloxycarbonyl)porphyrin 5 was determined X-ray analysis.
sci-hub.se 参考文章(30)
Maxence Urbani, Michael Grätzel, Mohammad Khaja Nazeeruddin, Tomás Torres, Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells Chemical Reviews. ,vol. 114, pp. 12330- 12396 ,(2014) , 10.1021/CR5001964
John T. Groves, William J. Kruper, Metalloporphyrins in Oxidative Catalysis. Oxygen Transfer Reactions of Oxochromium Porphyrins Israel Journal of Chemistry. ,vol. 25, pp. 148- 154 ,(1985) , 10.1002/IJCH.198500023
Tzong-Jin Wu, Nicholas H. Khoo, Fen Zhou, Brian J. Day, Dale A. Parks, Decreased hepatic ischemia-reperfusion injury by manganese–porphyrin complexes Free Radical Research. ,vol. 41, pp. 127- 134 ,(2007) , 10.1080/10715760600801298
Gavin O’Mahony, Andrew K. Pitts, Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups. Organic Letters. ,vol. 12, pp. 2024- 2027 ,(2010) , 10.1021/OL100507N
Andrew J. Saggiomo, Masaru Asai, Pauline M. Schwartz, Alcoholation of the trifluoromethyl group. I. Ortho esters derived from 1- and 3-trifluoromethylphenothiazines Journal of Heterocyclic Chemistry. ,vol. 6, pp. 631- 634 ,(1969) , 10.1002/JHET.5570060506
Kenji Kobayashi, Masayuki Koyanagi, Ken Endo, Hideki Masuda, Yasuhiro Aoyama, Self-Assembly of Porphyrin Arrays by Hydrogen Bonding in the Solid State: An Orthogonal Porphyrin–Bisresorcinol System Chemistry: A European Journal. ,vol. 4, pp. 417- 424 ,(1998) , 10.1002/(SICI)1521-3765(19980310)4:3<417::AID-CHEM417>3.0.CO;2-S
Hiroshi Kimoto, Louis A. Cohen, Fluorine reactivity in 2-(trifluoromethyl)imidazoles Journal of Organic Chemistry. ,vol. 10, pp. 2902- 2906 ,(1979) , 10.1021/JO01330A016
RICHARD CHARVET, JONATHAN P. HILL, YONGSHU XIE, YUTAKA WAKAYAMA, KATSUHIKO ARIGA, RECENT DEVELOPMENTS ON PORPHYRIN ASSEMBLIES COSMOS. ,vol. 04, pp. 141- 171 ,(2008) , 10.1142/S0219607708000342
Pilar Hidalgo Ramos, Alexander B. C. Deutman, Johannes A. A. W. Elemans, Roeland J. M. Nolte, Alan E. Rowan, Cyrille Monnereau, Porphyrin Macrocyclic Catalysts for the Processive Oxidation of Polymer Substrates Journal of the American Chemical Society. ,vol. 132, pp. 1529- 1531 ,(2010) , 10.1021/JA908524X
R. Mechoulam, S. Cohen, A. Kaluszyner, Notes - Basic Alcoholysis of the Trifluoromethyl Group in 1,1,1-Trifluoro-2,2-diarylethanes Journal of Organic Chemistry. ,vol. 21, pp. 801- 803 ,(1956) , 10.1021/JO01113A605