A convenient synthesis of fluorinated vinyl ethers derived from di-O-isopropylidenehexofuranose and O-isopropylidenepentofuranose
作者： Bartosz Marciniak , Monika Bilska-Markowska , Monika Grzeszczuk , Magdalena Rapp , Henryk Koroniak
DOI: 10.1016/J.JFLUCHEM.2014.06.013
关键词: Polymer chemistry 、 NMR spectra database 、 Coupling constant 、 Chemistry
摘要: Abstract This paper focuses on a convenient synthesis of fluorinated vinyl ethers derived from di- O -isopropylidenehexofuranose and -isopropylidenepentofuranose allyl alcohols. The structures new compounds have been confirmed by 1 H, 13 C 19 F NMR spectroscopic methods. An analysis coupling constants between vinylic H atoms observed in spectra has allowed assignment Z/E geometry the products.
sci-hub.se 参考文章(31)
Christiane Leibold, Stefan Reinemann, Rolf Minkwitz, Paul R. Resnik, Heinz Oberhammer, Effect of Fluorination on the Conformational Properties of Methyl Vinyl Ether Journal of Organic Chemistry. ,vol. 62, pp. 6160- 6163 ,(1997) , 10.1021/JO9705428
Katsuhiro Akiyama, Koichi Mikami, Enantioselective catalysis of Claisen rearrangement by DABNTf–Pd(II) complex Tetrahedron Letters. ,vol. 45, pp. 7217- 7220 ,(2004) , 10.1016/J.TETLET.2004.08.049
Magdalena Rapp, Monika Bilska, Henryk Koroniak, Fluorination of tertiary alcohols derived from di-O-isopropylidenehexofuranose and O-isopropylidenepentofuranose Journal of Fluorine Chemistry. ,vol. 132, pp. 1232- 1240 ,(2011) , 10.1016/J.JFLUCHEM.2011.07.001
William R. Dolbier, Guide to Fluorine NMR for Organic Chemists ,(2009)
Frédérique Tellier, Max Audouin, Raymond Sauvêtre, Synthesis of α-trifluoromethyl unsaturated acids and derivatives Journal of Fluorine Chemistry. ,vol. 113, pp. 167- 175 ,(2002) , 10.1016/S0022-1139(01)00542-5
Kwan Soo Kim, Jung Hee Kim, Young Kwan Kim, Yong Sun Park, Chi Sun Hahn, Synthesis of C-4 branched-chain furanoses by free radical-mediated cyclization Carbohydrate Research. ,vol. 194, pp. C1- C3 ,(1989) , 10.1016/0008-6215(89)85034-7
José Kovensky, Jean-Maurice Mallet, Jacques Esnault, Pierre-Alexandre Driguez, Philippe Sizun, Jean-Pascal Hérault, Jean-Marc Herbert, Maurice Petitou, Pierre Sinaÿ, Further Evidence for the Critical Role of a Non‐Chair Conformation of L‐Iduronic Acid in the Activation of Antithrombin European Journal of Organic Chemistry. ,vol. 2002, pp. 3595- 3603 ,(2002) , 10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F
Hajime Komura, Takashi Iwashita, Hideo Naoki, Koji Nakanishi, Jun Oka, Kunihiro Ueda, Osamu Hayaishi, Structure and synthesis of 3-deoxy-D-glycero-pentos-2-ulose, an unusual sugar produced enzymatically from (ADP-ribosyl)histone H2B Journal of the American Chemical Society. ,vol. 105, pp. 5164- 5165 ,(1983) , 10.1021/JA00353A069
Tadashi Narita, On the polymerization reactivity of fluorinated vinyl monomers Macromolecular Rapid Communications. ,vol. 21, pp. 613- 627 ,(2000) , 10.1002/1521-3927(20000601)21:10<613::AID-MARC613>3.0.CO;2-D
Z.S. Nurkeeva, I.S. Tyukova, A.I. Suvorova, G.A. Mun, A.B. Dzhusupbekova, V.V. Khutoryanskiy, Miscibility studies in poly(methyl vinyl ether)/hydroxypropylcellulose binary system in aqueous solutions and solid state Carbohydrate Polymers. ,vol. 62, pp. 80- 86 ,(2005) , 10.1016/J.CARBPOL.2005.06.023