STAUDINGER REACTION BETWEEN BICYCLIC PHOSPHITES AND AZIDES

被引:2
|
作者
LEI, GQ
XU, HT
XU, XL
机构
[1] Beijing Pharmaceutical Chemistry Institute, Beijing 102205, P. R.
关键词
STAUDINGER REACTION; BICYCLIC PHOSPHITE; IMINOPHOSPHATE;
D O I
10.1080/10426509208038337
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Staudinger reaction of 4-isopropyl bicyclic phosphite 1 with azides 2-5 to N-substituted bicyclic iminophosphates 8-11 is described. Attempts to obtain the corresponding bicyclic iminophosphates from 1 with azides 6 and 7 were unsuccessful. The microanalytical data, i.r., Raman, 31P n. m.r. and mass spectra of these bicyclic iminophosphates are also reported. The results show that the Staudinger reaction of bicyclic phosphites is more difficult than that of acyclic phosphites, bicyclic phosphites react only with azides (R-N3) in which R are strong electron-attracting groups. The mechanism of the reaction is discussed. © 1992, Taylor & Francis Group, LLC. All rights reserved.
引用
收藏
页码:101 / 106
页数:6
相关论文
共 50 条
  • [31] STEREOCHEMISTRY .50. N-PHOSPHORYLATED AZIRIDINES - REACTION OF 2-IODOALKYL AZIDES WITH PHOSPHINES AND PHOSPHITES
    HASSNER, A
    GALLE, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) : 3733 - &
  • [32] A REGIOSELECTIVE ENTRY TO AZIRINO[1,2-A]INDOLE DERIVATIVES BY EPOXIDATION/STAUDINGER REACTION OF ORTHO-ALLYLPHENYL AZIDES
    MOLINA, P
    ALAJARIN, M
    LOPEZLAZARO, A
    TETRAHEDRON LETTERS, 1992, 33 (17) : 2387 - 2390
  • [33] The reaction between actylene-by-magnesium-bromide and azides
    Kleinfeller, H
    Bonig, G
    JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1931, 132 (5/7): : 175 - 199
  • [34] Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction
    Malkinson, JP
    Falconer, RA
    Toth, I
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17): : 5249 - 5252
  • [35] Trapping of a phosphazide intermediate in the Staudinger reaction of tertiary phosphines with azides and its application to the synthesis of analogs of the marine alkaloid midpacamide
    Fresneda, PM
    Castañeda, M
    Sanz, MA
    Molina, P
    TETRAHEDRON LETTERS, 2004, 45 (08) : 1655 - 1657
  • [36] The acid and base catalysis in the reaction between dialkyl phosphites and iodine
    Nylen, P
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1938, 235 (03): : 161 - 182
  • [37] Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides
    Li, Xingzhuo
    Wang, Zhenguo
    Luo, Wenjun
    Wang, Zixu
    Yin, Keshu
    Li, Le
    MOLECULES, 2022, 27 (17):
  • [38] REACTION OF AZIDOLACTAM WITH PHOSPHITES
    DIMUKHAMETOV, MN
    NURETDINOV, IA
    ZHURNAL OBSHCHEI KHIMII, 1983, 53 (11): : 2648 - 2650
  • [39] REACTION OF SULPHUR DICHLORIDE WITH TRIALKYL PHOSPHITES AND DIALKYL PHOSPHITES
    MICHALSKI, J
    PLISZKA, B
    CHEMISTRY & INDUSTRY, 1962, (24) : 1052 - 1052
  • [40] REACTION OF PHOSPHITES WITH TRICHLOROACETONITRILES
    KUTYREV, AA
    MOSKVA, VV
    ALPAROVA, MV
    ZHURNAL OBSHCHEI KHIMII, 1984, 54 (07): : 1494 - 1499