TANDEM ENYNE ALLENE-RADICAL CYCLIZATION VIA [3,3]-SIGMATROPIC REARRANGEMENTS

被引：30
|
作者：
GRISSOM, JW
HUANG, DH
机构：
[1] Department of Chemistry, University of Utah, Salt Lake City
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期
关键词：
D O I：
10.1021/jo00097a002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enediynes 1, 7, 12, and 16 undergo a tandem [3,3] sigmatropic shift-enyne allene cyclization. Enediynes 7 and 16 are especially interesting because after undergoing a [3,3] sigmatropic shift and enyne allene cyclization, the resultant biradical undergoes a 5-exo radical cyclization. These reactions can be effected by either heating at 150 degrees C or by treatment with silver salts followed by heating at 75 degrees C.
引用
收藏
页码：5114 / 5116
页数：3
相关论文
共 50 条
  • [1] TANDEM ENEYNE ALLENE-RADICAL CYCLIZATION VIA [2,3] AND [3,3] SIGMATROPIC SHIFTS
    GRISSOM, JW
    HUANG, DH
    SLATTERY, BJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 416 - ORGN
  • [2] TANDEM ENEYNE ALLENE-RADICAL CYCLIZATION VIA [2,3]-SIGMATROPIC SHIFTS
    GRISSOM, JW
    SLATTERY, BJ
    TETRAHEDRON LETTERS, 1994, 35 (29) : 5137 - 5140
  • [3] TANDEM ENYNE ALLENE-RADICAL CYCLIZATION VIA BASE-CATALYZED ISOMERIZATION OF ENEDIYNE SULFONES
    GRISSOM, JW
    KLINGBERG, D
    TETRAHEDRON LETTERS, 1995, 36 (37) : 6607 - 6610
  • [4] CYCLIZATION-INDUCED [3,3]-SIGMATROPIC REARRANGEMENTS
    OVERMAN, LE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 235 - 235
  • [5] Tandem enyne allene-radical cyclization: Low-temperature approaches to benz[e]indene and indene compounds
    Grissom, JW
    Klingberg, D
    Huang, DH
    Slattery, BJ
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03): : 603 - 626
  • [6] LOW-TEMPERATURE TANDEM ENYNE ALLENE-RADICAL CYCLIZATION - IMPROVED SYNTHESIS OF 2,3-DIHYDROINDENES FROM SIMPLE ENEDIYNES
    GRISSOM, JW
    HUANG, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 77 - ORGN
  • [7] A free-radical approach to [3,3]-sigmatropic rearrangements.
    Enholm, EJ
    Moran, KM
    Whitley, PE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 444 - ORGN
  • [8] [3,3]-SIGMATROPIC REARRANGEMENTS OF FLUOROCARBANIONS
    ANDREEV, VG
    KOLOMIETS, AF
    FOKIN, AV
    JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (03) : 259 - 269
  • [9] COMPETITIVE [1,3]-SIGMATROPIC AND [3,3]-SIGMATROPIC REARRANGEMENTS
    ARNOLD, RT
    KULENOVIC, ST
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (05): : 891 - 894
  • [10] [3,3]-SIGMATROPIC REARRANGEMENTS OF FLUORINATED COMPOUNDS
    PURRINGTON, ST
    WEEKS, SC
    JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (02) : 165 - 173
12345