Photoinduced cycloadditions and cyclizations. Mechanistic studies and synthetic applications

被引:0
作者
Mattay, J
Albrecht, E
Fagnoni, M
Heidbreder, A
Hintz, S
Kirschberg, T
Klessinger, M
Mahlmann, J
Schlachter, I
Steenken, S
机构
[1] CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
[2] MAX PLANCK INST STRAHLENCHEM, D-45470 MULHEIM AN DER RUHR, GERMANY
来源
JOURNAL OF INFORMATION RECORDING | 1996年 / 23卷 / 1-2期
关键词
photoinduced electron transfer (PET); radical ions; C-C bond cleavage; cyclization; cycloaddition; nitrile ylides; laser flash photolysis; semiempirical calculations;
D O I
暂无
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Synthetic applications and mechanistic studies from three areas of photoinduced cycloadditions and cyclizations are reported: First it is shown that unsaturated silyl enol ethers preferentially cyclisize in a 6-endo mode via their photochemically generated radical cations. In the following chapter we discuss fragmentation-cyclization reactions of unsaturated alpha-cyclopropyl ketones by photoinduced electron transfer leading to polycyclic compounds. Finally a kinetic and theoretical study of [2+3] cycloadditions of nitrile ylides generated from 2H-azirines is presented.
引用
收藏
页码:23 / 29
页数:7
相关论文
共 28 条
  • [1] PHOTOINDUCED ELECTRON-TRANSFER (PET) IN ORGANIC-SYNTHESIS - [3+2)-TYPE CYCLOADDITION, CYCLIZATION AND C-C BOND-CLEAVAGE REACTIONS
    ALBRECHT, E
    AVERDUNG, J
    BISCHOF, EW
    BISCHOF, EW
    HEIDBREDER, A
    KIRSCHBERG, T
    MULLER, F
    MATTAY, J
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1994, 82 (1-3) : 219 - 232
  • [2] ALBRECHT E, J INF REC MATS, V21, P607
  • [3] ALBRECHT E, 1995, THESIS U MUNSTER
  • [4] RADICAL IONS AND PHOTOCHEMICAL CHARGE-TRANSFER PHENOMENA .29. RADICAL ANIONIC CYCLIZATION REACTIONS VIA PHOTOCHEMICALLY INDUCED ELECTRON-TRANSFER
    BISCHOF, EW
    MATTAY, J
    [J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7137 - 7140
  • [5] REGIOSELECTIVE AND STEREOSELECTIVE CYCLIZATIONS - APPLICATION TO NATURAL-PRODUCTS SYNTHESIS
    COSSY, J
    [J]. PURE AND APPLIED CHEMISTRY, 1992, 64 (12) : 1883 - 1888
  • [6] Eberson L., 1987, ELECT TRANSFER REACT
  • [7] FAGNONI M, UNPUB
  • [8] FOX MA, 1988, PHOTOINDUCED ELE A D
  • [9] RADICAL IONS AND PHOTOCHEMICAL CHARGE-TRANSFER PHENOMENA .34. PET-OXIDATIVE CYCLIZATION OF UNSATURATED ENOL SILYL ETHERS
    HEIDBREDER, A
    MATTAY, J
    [J]. TETRAHEDRON LETTERS, 1992, 33 (15) : 1973 - 1976
  • [10] HEIDBREDER A, 1994, THESIS U MUNSTER