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.
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1992年 / 66卷 / 1-4期
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
  • [11] Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
    Banik, BK
    Banik, I
    Becker, FF
    BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (11) : 3611 - 3622
  • [12] Asymmetric synthesis of anticancer β-lactams via Staudinger reaction
    Banik, Bimal K.
    Samajdar, Susanta
    Becker, Frederick F.
    MOLECULAR MEDICINE REPORTS, 2010, 3 (02) : 319 - 321
  • [13] Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
    Banik, BK
    Becker, FF
    TETRAHEDRON LETTERS, 2000, 41 (34) : 6551 - 6554
  • [14] Theoretical studies on selectivities in the Staudinger reaction of vicinal diimines and ketenes
    HOU ShiLi
    LI XinYao
    XU JiaXi
    Science China(Chemistry), 2013, (03) : 370 - 439
  • [15] Staudinger reaction at in-bridgehead positions of phosphorus macrobicyclic compounds
    Bauer, I
    Gruner, M
    Goutal, S
    Habicher, WD
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (16) : 4011 - 4016
  • [16] γ-heteroatom directed stereocontrolled Staudinger cycloaddition reaction of vinylketenes and imines
    Shaikh, Aarif L.
    Puranik, Vedavati G.
    Deshmukh, A. R. A. S.
    TETRAHEDRON LETTERS, 2006, 47 (33) : 5993 - 5996
  • [17] Theoretical studies on selectivities in the Staudinger reaction of vicinal diimines and ketenes
    ShiLi Hou
    XinYao Li
    JiaXi Xu
    Science China Chemistry, 2013, 56 : 370 - 379
  • [18] Janus carbosilane/phosphorhydrazone dendrimers synthesized by the 'click' Staudinger reaction
    Gottis, Sebastien
    Rodriguez, Lara-Isabel
    Laurent, Regis
    Angurell, Inmaculada
    Seco, Miquel
    Rossell, Oriol
    Majoral, Jean-Pierre
    Caminade, Anne-Marie
    TETRAHEDRON LETTERS, 2013, 54 (50) : 6864 - 6867
  • [19] Theoretical studies on selectivities in the Staudinger reaction of vicinal diimines and ketenes
    Hou ShiLi
    Li XinYao
    Xu JiaXi
    SCIENCE CHINA-CHEMISTRY, 2013, 56 (03) : 370 - 379
  • [20] Diastereoselective synthesis of spiro-β-lactams via Staudinger reaction
    Rojas-Lima, Susana
    Santillan-Sid, Lidia
    Lopez-Ruiz, Heraclio
    Alvarez-Hernandez, Alejandro
    HETEROCYCLES, 2007, 71 (03) : 531 - 542