α-aminophosphonates bearing free hydroxyl groups in the aromatic rings.: Synthesis and NMR characterization

被引:7
|
作者
Failla, S
Finocchiaro, P
Hagele, G
Kalchenko, VI
机构
[1] Univ Catania, Fac Ingn, Ist Chim, I-95125 Catania, Italy
[2] Univ Dusseldorf, Inst Anorgan Chem & Strukturchem, D-40225 Dusseldorf, Germany
[3] Natl Acad Sci Ukraine, Inst Organ Chem, UA-253660 Kiev, Ukraine
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1997年 / 128卷
关键词
metal chelating phosphonates; NMR and FAB-MS characterization; monomers for polycondensates;
D O I
10.1080/10426509708031564
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In this paper we describe a useful synthetic procedure leading in very good yields to mono- and bis-alpha-aminophosphonic acid dialkylesters containing the free phenolic hydroxyl group in a strategic position of the aromatic ring in order to enhance complexation with metal ions. This synthetic procedure is based on the addition of a solution of sodium dialkyl phosphite in phosphite to imine precursors. The addition reaction is highly stereospecific: only one diastereomer for each of the bis-alpha-aminophosphonic acid dialkylesters is formed. All compounds were characterized by NMR (H-1 and P-31) and by FAB-MS spectroscopy.
引用
收藏
页码:63 / 77
页数:15
相关论文
共 50 条
  • [1] Synthesis and characterization of novel potentially biodegradable aromatic polyesters consisting of divanillic acids with free phenolic hydroxyl groups
    Fujieda, Kentaro
    Enomoto, Yukiko
    Zhang, Yunfan
    Iwata, Tadahisa
    POLYMER, 2022, 257
  • [2] Biodegradable amphiphilic block copolymers bearing protected hydroxyl groups: Synthesis and characterization
    Hu, Xiuli
    Liu, Shi
    Chen, Xuesi
    Mo, Guojun
    Xie, Zhigang
    Jing, Xiabin
    BIOMACROMOLECULES, 2008, 9 (02) : 553 - 560
  • [3] Synthesis and Characterization of Polythiophenes Bearing Aromatic Groups at the 3-Position
    Ohshimizu, Kaoru
    Takahashi, Ayumi
    Rho, Yecheol
    Higashihara, Tomoya
    Ree, Moonhor
    Ueda, Mitsuru
    MACROMOLECULES, 2011, 44 (04) : 719 - 727
  • [4] STRUCTURAL CHARACTERIZATION OF ACTIVATING AND DEACTIVATING GROUPS IN AROMATIC RINGS
    HAROCASTELLANOS, JA
    GOMEZGAYTAN, E
    URBINADURAN, JE
    RUIZLOYOLA, B
    LOPEZCELIS, I
    CRUZSOSA, F
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 96 - CHED
  • [5] Facile synthesis and characterization of novel biodegradable amphiphilic block copolymers bearing pendant hydroxyl groups
    Hu, Gaicen
    Fan, Xiaoshan
    Xu, Bingcan
    Zhang, Delong
    Hu, Zhiguo
    MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2014, 43 : 207 - 213
  • [6] Polyurethanes with pendant hydroxyl groups:: Synthesis and characterization
    Ubaghs, L
    Fricke, N
    Keul, H
    Höcker, H
    MACROMOLECULAR RAPID COMMUNICATIONS, 2004, 25 (03) : 517 - 521
  • [7] Synthesis of porphyrins with reactive groups on phenyl rings. 8. Azo dyes on tetraphenylporphyrins
    Syrbu, S.A.
    Semeikin, A.S.
    Syrbu, T.V.
    Chemistry of Heterocyclic Compounds, 1996, 32 (08): : 897 - 901
  • [8] Synthesis and properties of amphiphilic BODIPY derivatives bearing hydroxyl groups
    Vincent, Matthew
    Beabout, Eva
    Bennett, Richard
    Hewavitharanage, Priya
    TETRAHEDRON LETTERS, 2013, 54 (16) : 2050 - 2054
  • [9] Well-defined polythioethers and polyethers containing pyridine rings. Synthesis and characterization
    Romdhane, H.B.
    de Leuze, A.
    Boileau, S.
    Bartholin, M.
    Sillion, B.
    Polymer Preprints, Division of Polymer Chemistry, American Chemical Society, 1992, 33 (01):
  • [10] Synthesis and Biological Activity of Steroids Bearing Aromatic Rings and Heterocycles
    Cui Jianguo
    Liu Liang
    Gan Chunfang
    Xiao Qi
    Huang Yanmin
    PROGRESS IN CHEMISTRY, 2014, 26 (2-3) : 320 - 333