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
  • [41] KINETIC INVESTIGATION OF THE REACTION BETWEEN DIALKYL PHOSPHITES AND AMINE HYDROCHLORIDES
    TROEV, K
    TASHEV, E
    BORISOV, G
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1982, 13 (03): : 359 - 362
  • [42] Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines
    Arrieta, A
    Lecea, B
    Cossío, FP
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17): : 5869 - 5876
  • [43] 60 YEARS OF STAUDINGER REACTION
    GOLOLOBOV, YG
    ZHMUROVA, IN
    KASUKHIN, LF
    TETRAHEDRON, 1981, 37 (03) : 437 - 472
  • [44] CHIRAL CONTROL OF THE STAUDINGER REACTION
    COOPER, RDG
    DAUGHERTY, BW
    BOYD, DB
    PURE AND APPLIED CHEMISTRY, 1987, 59 (03) : 485 - 492
  • [45] Redox reaction between benzyl azides and aryl azides: concerted synthesis of aryl nitriles and anilines
    Kim, Yongjin
    Rhee, Young Ho
    Park, Jaiwook
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (07) : 1636 - 1641
  • [46] REACTION OF TRIMETHYLSILYLDIETHYL PHOSPHITES AND DIETHYLACETYL PHOSPHITES WITH FLUORINATED KETONES
    KIBARDIN, AM
    GAZIZOV, TK
    PUDOVIK, AN
    ZHURNAL OBSHCHEI KHIMII, 1975, 45 (09): : 1982 - 1984
  • [47] Role of imine isomerization in the stereocontrol of the Staudinger reaction between ketenes and imines
    Cossio, Fernando P.
    de Cozar, Abel
    Sierra, Miguel A.
    Casarrubios, Luis
    Muntaner, Jaime G.
    Banik, Bimal K.
    Bandyopadhyay, Debasish
    RSC ADVANCES, 2021, 12 (01) : 104 - 117
  • [48] RECENT ADVANCES IN THE STAUDINGER REACTION
    GOLOLOBOV, YG
    KASUKHIN, LF
    TETRAHEDRON, 1992, 48 (08) : 1353 - 1406
  • [49] Synthesis of triphenylphosphazoperiindenones by staudinger reaction
    Belov, S. P.
    Komlev, I. V.
    Kuznetsov, S. V.
    Nifant'ev, E. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (12) : 2698 - 2699
  • [50] Synthesis of triphenylphosphazoperiindenones by staudinger reaction
    S. P. Belov
    I. V. Komlev
    S. V. Kuznetsov
    E. E. Nifant’ev
    Russian Journal of General Chemistry, 2009, 79 : 2698 - 2699
12345