Cyclobutylcarbinyl Radical Fragmentation Reactions of Tetronate [2+2] Photocycloaddition Products

被引：10
|
作者：
Hehn, Joerg P. [1 ]
Kemmler, Michael [1 ]
Bach, Thorsten [1 ]
机构：
[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany
来源：
SYNLETT | 2009年 / 08期
关键词：
cycloadditions; free radicals; photochemistry; ring expansion; ring opening; TRIS(TRIMETHYLSILYL)SILANE; REGIOSELECTIVITY; DERIVATIVES;
D O I：
10.1055/s-0029-1216728
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclobutanes derived from [2+2] photocycloaddition reactions of tetronic acid esters were subjected to free-radical fragmentation reactions. The product formation was strongly dependent oil the relative stabilities of the intermediate radicals, thus leading to either all oxepane or a methylenetetrahydrofuran in good yields.
引用
收藏
页码：1281 / 1284
页数：4
相关论文
共 50 条
  • [1] [2+2]-PHOTOCYCLOADDITION/FRAGMENTATION STRATEGIES FOR THE SYNTHESIS OF NATURAL AND UNNATURAL PRODUCTS
    WINKLER, JD
    BOWEN, CM
    LIOTTA, F
    CHEMICAL REVIEWS, 1995, 95 (06) : 2003 - 2020
  • [2] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION .4. SYNTHESIS OF [4.N]CYCLOPHANES BY [2+2] PHOTOCYCLOADDITION AND BIRCH REDUCTION - A RARE FRAGMENTATION OF TETRAMETHYLENE RADICAL-ANION
    NISHIMURA, J
    OHBAYASHI, A
    UEDA, E
    OKU, A
    CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (11): : 2025 - 2028
  • [3] Use of photoredox catalysis in [2+2] photocycloaddition reactions
    White, Michelle N.
    McMahon, Kevin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [4] Enantioselective intramolecular [2+2]-photocycloaddition reactions in solution
    Bach, Thorsten
    Bergmann, Hermann
    Harms, Klaus
    Angewandte Chemie (International Edition in English), 2000, 39 (13): : 2302 - 2304
  • [5] Enantioselective intramolecular [2+2]-photocycloaddition reactions in solution
    Bach, T
    Bergmann, H
    Harms, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (13) : 2302 - 2304
  • [6] Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis
    Bach, T
    SYNTHESIS-STUTTGART, 1998, (05): : 683 - 703
  • [7] [2+2]-PHOTOCYCLOADDITION REACTIONS OF AROMATIC THIONECARBONATES WITH ALKENES AND DIENES
    GOTTHARD.H
    LISTL, M
    CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (08): : 2552 - 2557
  • [8] Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions
    Fort, Diego A.
    Woltering, Thomas J.
    Nettekoven, Matthias
    Knust, Henner
    Bach, Thorsten
    CHEMICAL COMMUNICATIONS, 2013, 49 (29) : 2989 - 2991
  • [9] [2+2]-Photocycloaddition Reactions of Tetronic Acid Esters and Amides
    Hehn, Joerg P.
    Gamba-Sanchez, Diego
    Kemmler, Michael
    Fleck, Martin
    Basler, Birte
    Bach, Thorsten
    SYNTHESIS-STUTTGART, 2010, (13): : 2308 - 2312
  • [10] [2+2] photocycloaddition of tetronates
    Kemmler, M
    Bach, T
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) : 4824 - 4826
12345