SYNTHESIS OF A 2H-AZIRINE BY [1+2]-CYCLOADDITION OF A PHOSPHINOCARBENE WITH A NITRILE AND ITS RING-EXPANSION TO A 1,2-LAMBDA(5)-AZAPHOSPHETE

被引:50
作者
ALCARAZ, G [1 ]
WECKER, U [1 ]
BACEIREDO, A [1 ]
DAHAN, F [1 ]
BERTRAND, G [1 ]
机构
[1] CNRS,CHIM COORDINAT LAB,F-31077 TOULOUSE,FRANCE
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 11期
关键词
CARBENES; CYCLOADDITIONS; HETEROCYCLES; PHOSPHORUS COMPOUNDS;
D O I
10.1002/anie.199512461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new type of carbene reaction is observed with the stable phosphinocarbene 1. It reacts with benzonitrile to give the 2H‐azirine 2, which in dichloromethane is converted into the 1,2λ5‐azaphosphete 3 after addition of a catalytic amount of dichloro(p‐cymene)ruthenium(II). R = (c‐C6H11)2N. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1246 / 1248
页数:3
相关论文
共 39 条
  • [1] SYNTHESIS AND EVOLUTION OF PHOSPHANYLCARBENE BORANE ADDUCTS
    ALCARAZ, G
    REED, R
    BACEIREDO, A
    BERTRAND, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (17) : 1354 - 1355
  • [2] ELECTRON-DISTRIBUTION IN A STABLE CARBENE
    ARDUENGO, AJ
    DIAS, HVR
    DIXON, DA
    HARLOW, RL
    KLOOSTER, WT
    KOETZLE, TF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6812 - 6822
  • [3] A STABLE CRYSTALLINE CARBENE
    ARDUENGO, AJ
    HARLOW, RL
    KLINE, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 361 - 363
  • [4] CHEMICAL SHIELDING TENSER OF A CARBENE
    ARDUENGO, AJ
    DIXON, DA
    KUMASHIRO, KK
    LEE, C
    POWER, WP
    ZILM, KW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6361 - 6367
  • [5] PHOTOELECTRON-SPECTROSCOPY OF A CARBENE/SILYLENE/GERMYLENE SERIES
    ARDUENGO, AJ
    BOCK, H
    CHEN, H
    DENK, M
    DIXON, DA
    GREEN, JC
    HERRMANN, WA
    JONES, NL
    WAGNER, M
    WEST, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6641 - 6649
  • [6] ARDUENGO AJ, 1992, J AM CHEM SOC, V114, P4430
  • [7] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE
    BENNETT, MA
    SMITH, AK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02): : 233 - 241
  • [8] SYNTHESIS AND REACTIVITY OF CYCLIC 6-MEMBERED 6-PI-MEMBERED AND 4-MEMBERED 4-PI-ELECTRON YLIDES
    BIEGER, K
    TEJEDA, J
    REAU, R
    DAHAN, F
    BERTRAND, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) : 8087 - 8094
  • [9] DEFORMATION DENSITY OF A DIAZIRINE RING IN THE X-RAY STRUCTURE OF 3-[(PARA-NITROPHENOXY)METHYL]-3-CHLORODIAZIRINE
    CAMERON, TS
    BAKSHI, PK
    BORECKA, B
    LIU, MTH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1889 - 1890