NITRILE IMINES - FROM MATRIX CHARACTERIZATION TO STABLE COMPOUNDS

被引:110
作者
BERTRAND, G [1 ]
WENTRUP, C [1 ]
机构
[1] UNIV QUEENSLAND,DEPT CHEM,BRISBANE,QLD 4072,AUSTRALIA
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 05期
关键词
D O I
10.1002/anie.199405271
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The concept of 1,3‐dipolar cycloaddition was developed, starting in the late 1950s, largely by Rolf Huisgen and his students in Munich, and it has led to one of the most versatile methods for the construction of five‐membered ring heterocycles. Although first known only as transient intermediates, nitrile imines have been at the heart of mechanistic studies of this type of cycloaddition reactions. Hundreds of mechanistic papers appeared in 1960s and 1970s; reliable spectroscopic observations were achieved in the early 1980s both at low temperatures and in the gas phase; finally, the first crystalline nitrile imine was reported in 1988. The unusual structures found by X‐ray analyses as well as the facile rearrangements observed experimentally have fostered a new interplay between experiment and theory. The story of nitrile imines, from matrix characterization to stable compounds, nicely illustrates the role that main group elements can play in organic chemistry. Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:527 / 545
页数:19
相关论文
共 166 条
  • [31] THE SURPRISINGLY FACILE DEHYDROHALOGENATION OF A HYDRAZONOYL CHLORIDE INTO A STABLE PHOSPHORUS-SUBSTITUTED NITRILIMINE
    CASTAN, F
    BACEIREDO, A
    DAHAN, F
    AUNER, N
    BERTRAND, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) : 1274 - 1276
  • [32] SYNTHESIS AND REACTIVITY OF STABLE SILYL-SUBSTITUTED NITRILIMINES
    CASTAN, F
    BACEIREDO, A
    BIGG, D
    BERTRAND, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1801 - 1807
  • [33] STABLE N-PHOSPHANYL NITRILIMINES - REACTIVITY ON THE PERIPHERY OF THE NITRILIMINE SKELETON
    CASTAN, F
    GRANIER, M
    STRAW, TA
    BACEIREDO, A
    DILLON, KB
    BERTRAND, G
    [J]. CHEMISCHE BERICHTE, 1991, 124 (08) : 1739 - 1746
  • [34] CASTAN F, 1989, ANGEW CHEM, V101, P1253
  • [35] 1-AZA-1,2,4,6-CYCLOHEPTATETRAENE
    CHAPMAN, OL
    LEROUX, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) : 282 - 285
  • [36] 1,3-DIPOLAR CYCLO-ADDITIONS .89. NEW CONTRIBUTIONS TO THE CHEMISTRY OF DIPHENYLNITRILIMINE
    CLOVIS, JS
    FLIEGE, W
    HUISGEN, R
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (09): : 3062 - 3070
  • [37] A MULTI-NUCLEAR MAGNETIC-RESONANCE STUDY OF NITRILE OXIDES
    DESARLO, F
    BRANDI, A
    GUARNA, A
    NICCOLAI, N
    [J]. JOURNAL OF MAGNETIC RESONANCE, 1982, 50 (01) : 64 - 70
  • [38] DUBAU N, UNPUB
  • [39] 1.3-DIPOLARE CYCLOADDITIONEN .31. DIPOLAROPHILEN-AKTIVITATEN GEGENUBER DIPHENYLNITRILIMIN UND ZAHLENMASSIGE ERMITTLUNG DER SUBSTITUENTENEINFLUSSE
    ECKELL, A
    HUISGEN, R
    SUSTMANN, R
    WALLBILL.G
    GRASHEY, D
    SPINDLER, E
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (07): : 2192 - &
  • [40] HCN DIMERS - IMINOACETONITRILE AND N-CYANOMETHANIMINE
    EVANS, RA
    LORENCAK, P
    HA, TK
    WENTRUP, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7261 - 7276