P2O5-MsOH mediated regioselective diaroylation of 2,2′-dimethoxy-1,1′-binaphthyl

被引:13
|
作者
Maeyama, K [1 ]
Ogura, K
Okamoto, A
Sakurai, K
Yoshida, Y
Ogino, K
Yonezawa, N
机构
[1] Tokyo Univ Agr & Technol, Dept Organ & Polymer Mat Chem, Tokyo, Japan
[2] Toyo Univ, Dept Appl Chem, Kawagoe, Saitama 350, Japan
[3] Tokyo Univ Agr & Technol, Grad Sch Bioapplicat & Syst Engn, Tokyo, Japan
关键词
2,2 '-dimethoxy-1,1 '-binaphthyl; direct condensation; phosphorous pentoxide-methanesulfonic acid; regioselective diarylation;
D O I
10.1081/SCC-200028641
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphorus pentoxide-methanesulfonic acid (P2O5-MsOH) mediated electrophilic aromatic substitution diaroylation of 2,2'-dimethoxy-1,1'-binaphthyl (1) with several aromatic carboxylic acids (3) proceeds to afford 6,6'-diaroylated adducts (4) as single regioisomers.
引用
收藏
页码:3243 / 3250
页数:8
相关论文
共 50 条
  • [1] SPONTANEOUS RESOLUTION OF 2,2'-DIMETHOXY-1,1'-BINAPHTHALENE
    GOTTARELLI, G
    SPADA, GP
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06): : 2096 - 2098
  • [2] Improved synthesis of 2,2′-dimethoxy-1,1′-binaphthyl-3,3′-diacetic acid derivatives
    Zrig, S
    Andrioletti, B
    Rose, E
    Colin, J
    TETRAHEDRON LETTERS, 2005, 46 (07) : 1103 - 1105
  • [3] THE CRYSTAL AND MOLECULAR-STRUCTURE OF 2,2'-DIMETHOXY-1,1'-DINAPHTHYL
    GRIDUNOVA, GV
    SHKLOVER, VE
    STRUCHKOV, YT
    CHAYANOV, BA
    KRISTALLOGRAFIYA, 1983, 28 (01): : 87 - 91
  • [4] SYNTHESIS OF (R)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2'-DIMETHOXY-1,1'-BINAPTHYL AND (S)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL, A NEW AXIALLY DISSYMMETRIC BIS(TRIARYLPHOSPHINE)
    HORIUCHI, T
    OHTA, T
    STEPHAN, M
    TAKAYA, H
    TETRAHEDRON-ASYMMETRY, 1994, 5 (03) : 325 - 328
  • [5] 2,2′-dimethoxy-1,1′-binaphthyl-3,3′-diboronic acid, a versatile intermediate in the synthesis of 3,3′-diaryl substituted binaphthyl derivatives
    Kratky, P
    Haslinger, U
    Widhalm, M
    MONATSHEFTE FUR CHEMIE, 1998, 129 (12): : 1319 - 1327
  • [6] Synthesis and Characterization of Two Pb(II) Complexes of 2,2′-dihydroxy, Dimethoxy-1,1′-binaphthyl-3,3′-dicarboxylic Acid
    Li, Li-Jun
    Liu, Chuan-Chuan
    Sun, Ming-Zhen
    Qiao, Yu
    Huang, Ying-Ying
    Du, Jian-Long
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2014, 593 (01) : 187 - 200
  • [7] Optically Active Helical Polymer From Anionic Polymerization of (S)-6-Acrylyl-2,2′-dimethoxy-1,1′-binaphthyl
    Chen, Yehui
    Yang, Liwen
    Yang, Nianfa
    Yang, Zhusheng
    JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, 2014, 51 (08): : 633 - 638
  • [8] 2,2′-Dimethoxy-1,1′-binaphthyl-3,3′-diboronic Acid, a Versatile Intermediate in the Synthesis of 3,3′-Diaryl Substituted Binaphthyl Derivatives2,2′-Dimethoxy-1,1′-binaphthyl-3,3′-diborsäure, ein vielseitiges Zwischenprodukt in der Synthese 3,3′-diarylsubstituierter Binaphthylderivate
    Petra Kratky
    Ulrike Haslinger
    Michael Widhalm
    Monatshefte für Chemie / Chemical Monthly, 1998, 129 (12) : 1319 - 1327
  • [9] Nickel complex-mediated synthesis of optically active wholly aromatic polyketones bearing 2,2′-dimethoxy-1,1′-binaphthyl-6,6′-ene units
    Maeyama, K
    Ogura, K
    Okamoto, A
    Ogino, K
    Saito, H
    Yonezawa, N
    POLYMER JOURNAL, 2005, 37 (10) : 736 - 741
  • [10] Nickel Complex-Mediated Synthesis of Optically Active Wholly Aromatic Polyketones Bearing 2,2′-Dimethoxy-1,1′-binaphthyl-6,6′-ene Units
    Katsuya Maeyama
    Kashiko Ogura
    Akiko Okamoto
    Kenji Ogino
    Hiromu Saito
    Noriyuki Yonezawa
    Polymer Journal, 2005, 37 : 736 - 741