GENERATION OF VINYLCARBENES BY THE INTRAMOLECULAR ADDITION OF ALPHA-DIAZO KETONES TO ACETYLENES

被引:76
作者
PADWA, A
CHIACCHIO, U
GARREAU, Y
KASSIR, JM
KRUMPE, KE
SCHOFFSTALL, AM
机构
[1] Department of Chemistry, Emory University, Atlanta
[2] Department of Chemistry, Universita di Catania, Catania
关键词
D O I
10.1021/jo00289a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: Treatment of several a-diazo alkynyl substituted ketones with rhodium(II) carboxylates results in intramolecular addition to the acetylenic 7r-bond to give a transient cyclopropene which spontaneously rearranges to a vinyl carbene intermediate. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:414 / 416
页数:3
相关论文
共 32 条
  • [1] ALDULAYYMI J, 1988, TETRAHEDRON LETT, P6149
  • [2] [Anonymous], 1980, REARRANGEMENTS GROUN
  • [3] ELECTRONIC EXCITED-STATES OF SMALL RING COMPOUNDS 3 - CYCLOPROPENE, VINYLCARBENE, AND VINYLMETHYLENE
    ARNOLD, DR
    HUMPHREYS, RW
    LEIGH, WJ
    PALMER, GE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (20) : 6225 - 6233
  • [4] ARNOLD DR, 1973, J AM CHEM SOC, V95, P7536
  • [5] BAIRD MS, 1988, TOP CURR CHEM, V144, P138
  • [6] BAIRD MS, 1984, TETRAHEDRON LETT, P1509
  • [7] GARDNER PD, 1967, J AM CHEM SOC, V89, P5425
  • [8] HALTON B, 1988, CHEM CYCLOPROPANES, V2
  • [9] HASHEM A, 1984, TETRAHEDRON, V40, P2003
  • [10] HAUCK G, 1981, J CHEM RES-S, P180