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Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5,10,15-triarylporphyrin radicals and their intramolecular cyclizations perfluoroalkyl iodides
Alternative Title卟啉氟烷基化: 2-和20-全氟烷基卟啉自由基的产生及其分子内环化反应
Chen L(陈亮); Jin LM(金利美); Guo CC(郭灿城); Chen QY(陈庆云)
2005
Source PublicationSynlett
ISSN0936-5214
Issue6Pages:963-970
AbstractTreatment of 5,10,15-triarylporphyrin (1) with perfluoroalkyl iodides (RfI,2) in the presence of Na2SO4/NaHCO3 in DMSO-CH2Cl2 at 65 degrees C for 3 hours gave a mixture of 2-polyfluoroalkyl-5,10,15-triarylporphyrins 3 and 5,10,15-triaryl-20-polyfluoroalkylporphyrins 4. When 1,3-diiodohexafluoropropane (2e) was reacted under the same conditions for 8 hours, the products were 5,10,15-triaryl-2,20-(hexafluoropropanediyl)porphyrins 5. Both 3e and 4e afforded the, same compounds 5 at 65 degrees C after a reaction time of 6 hours. Either 2-(2-chlorotetrafluoroethyl)-5,10,15-triphenylporphinato zinc(II) (Zn3aa) or 5,10,15-triphenyl-20-(2-chlorotetrafluoroethyl)porphinato zinc(H) (Zn4aa) resulted in 5,10,15-triaryl-2,20-(tetrafluoroethanecliyl)porphinato zinc(II) (Zn7) in excess Na2S2O,/NaHCO3 in DMSO-CH2Cl2 at 100 degrees C after 3 hours. Both Zn5a and Zn7 can be hydrolyzed quantitatively to 5,10,15-triaryl-2,20-(20'-oxo)(tetrafluoropropanediyl)porphinato zinc(II) (Zn8) and 5,10,15-trilphenyl-2,20-(20'-oxo)(difluoro-ethanediyl)porphinato zinc(II) (Zn9), respectively in the presence of silica gel at room temperature.
Subject Area有机氟化学
Department上海有机化学研究所元素有机化学研究室; 河南大学
URL查看原文
Indexed BySCI
Language英语
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/13600
Collection中科院有机氟化学重点实验室
Corresponding AuthorGuo CC(郭灿城); Chen QY(陈庆云)
Recommended Citation
GB/T 7714
Chen L,Jin LM,Guo CC,et al. Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5,10,15-triarylporphyrin radicals and their intramolecular cyclizations perfluoroalkyl iodides[J]. Synlett,2005(6):963-970.
APA 陈亮,金利美,郭灿城,&陈庆云.(2005).Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5,10,15-triarylporphyrin radicals and their intramolecular cyclizations perfluoroalkyl iodides.Synlett(6),963-970.
MLA 陈亮,et al."Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5,10,15-triarylporphyrin radicals and their intramolecular cyclizations perfluoroalkyl iodides".Synlett .6(2005):963-970.
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