Unexpected dual orbital effects in radical addition reactions involving acyl, silyl and related radicals

被引：26
|
作者：
Schiesser, CH [1 ]
Matsubara, H
Ritsner, I
Wille, U
机构：
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Bio21 Mol Sci & Biotechnol Inst, Melbourne, Vic, Australia
[3] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan
来源：
CHEMICAL COMMUNICATIONS | 2006年 / 10期
关键词：
D O I：
10.1039/b515330a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Molecular orbital calculations reveal that acyl and silyl radicals add to numerous types of pi-systems through simultaneous SOMO-LUMO and LUMO-HOMO interactions of the radical with the radicalophile respectively.
引用
收藏
页码：1067 / 1069
页数：3
相关论文
共 50 条
  • [1] Radicals masquerading as electrophiles: Dual orbital effects in nitrogen-philic acyl radical cyclization and related addition reactions
    Schiesser, Carl H.
    Wille, Uta
    Matsubara, Hiroshi
    Ryu, Ilhyong
    ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (05) : 303 - 313
  • [2] TANDEM FREE-RADICAL ALKENE ADDITION-REACTIONS OF ACYL RADICALS
    BOGER, DL
    MATHVINK, RJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4003 - 4008
  • [3] TANDEM FREE RADICAL-ALKENE ADDITION-REACTIONS OF ACYL RADICALS
    BOGER, DL
    MATHVINK, RJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 324 - ORGN
  • [4] Computational Studies of Reactions Involving Acyl Radicals
    Matsubara, Hiroshi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (09) : 1018 - 1031
  • [5] Electronic and steric effects of various silyl groups in radical addition reactions
    Hwu, JR
    King, KY
    Wu, IF
    Hakimelahi, GH
    TETRAHEDRON LETTERS, 1998, 39 (22) : 3721 - 3724
  • [6] Dual orbital effects in N-philic cyclizations of silyl radicals onto imines
    Wille, Uta
    Mucke, Eva-Katrin
    CHEMISTRY LETTERS, 2007, 36 (02) : 300 - 301
  • [7] ELECTRON RESONANCE STUDY OF SOME REACTIONS INVOLVING SILYL RADICALS
    BOWLES, AJ
    HUDSON, A
    JACKSON, RA
    JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (10): : 1947 - &
  • [8] ADDITION-REACTIONS OF SILYL RADICALS TO UNSATURATED-COMPOUNDS
    ALBERTI, A
    PEDULLI, GF
    REVIEWS OF CHEMICAL INTERMEDIATES, 1987, 8 (02): : 207 - 246
  • [9] Research Progress of Radical Reactions Involving Silyl Enol Ethers
    Luo, Zhaoyang
    Zhou, Weiwei
    Jun, Zhou
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (09) : 2658 - 2681
  • [10] Effects of α-tocopherol and related compounds on reactions involving various organic radicals
    Povalishev, VN
    Polozov, GI
    Shadyro, OI
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (05) : 1236 - 1239
12345