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
  • [21] One-pot synthesis of glycosyl amides from glycosyl azides using a modified Staudinger reaction
    Maunier, V
    Boullanger, P
    Lafont, D
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (02) : 231 - 235
  • [22] INTERMEDIATES IN REACTION BETWEEN ACYL AZIDES AND OLEFINS
    BAILEY, AS
    WHITE, JE
    CHEMISTRY & INDUSTRY, 1965, (38) : 1628 - &
  • [23] Diastereoselective synthesis of highly constrained spiro-β-lactams by the staudinger reaction using an unsymmetrical bicyclic ketene
    Trabocchi, Andrea
    Lalli, Claudia
    Guarna, Francesco
    Guarna, Antonio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (27) : 4594 - 4599
  • [24] Sequence of reactant combination alters the course of the Staudinger reaction of azides with acyl derivatives. Bimanes .30.
    Shalev, DE
    Chiacchiera, SM
    Radkowsky, AE
    Kosower, EM
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05): : 1689 - 1701
  • [25] Examining 1,4,2-Dioxazol-5-One as an Alternative Reagent to Acyl Azides in the Staudinger Reaction
    Zhang, Qianlan
    Liu, Shijie
    Xie, Yunzhi
    Du, Tianlei
    Wang, Shuaihao
    Guan, Jia
    Li, Jian
    Tang, Hao
    Zhou, Zijun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (47)
  • [26] Aryl azides in the traceless Staudinger ligation: Applications to prodrug synthesis
    Kirby, Thomas Price
    Koch, Tad H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [27] Dynamics of the Staudinger reaction
    Tian, WQ
    Wang, YA
    JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2005, 1 (03) : 353 - 362
  • [28] REACTION BETWEEN SODIUM DIALKYL PHOSPHITES AND DIALKYL PHOSPHOROCHLORIDATES
    STEC, W
    ZWIERZAK, A
    MICHALSK.J
    BULLETIN DE L ACADEMIE POLONAISE DES SCIENCES-SERIE DES SCIENCES CHIMIQUES, 1970, 18 (01): : 23 - &
  • [29] Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
    Kiick, KL
    Saxon, E
    Tirrell, DA
    Bertozzi, CR
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) : 19 - 24
  • [30] REACTION OF ARYLIDENEPROPYLAMINES WITH DIPHENYL PHOSPHITES AND DIALKYL PHOSPHITES
    BALYKOVA, IA
    PAK, VD
    KOZLOV, NS
    ZHURNAL OBSHCHEI KHIMII, 1974, 44 (11): : 2432 - 2434