Merging of 4+2 and 2+4 cycloaddition paths in the regiospecific dimerization of methacrolein. A case of concerted crypto-diradical cycloaddition

被引：31
|
作者：
Toma, L
Romano, S
Quadrelli, P
Caramella, P
机构：
[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
[2] Univ Pavia, Ist Nazl Fis Mat, I-27100 Pavia, Italy
[3] Univ Pavia, Dipartimento Fis A Volta, I-27100 Pavia, Italy
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 30期
关键词：
methacrolein; dimerization; secondary orbital interactions;
D O I：
10.1016/S0040-4039(01)00891-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regiospecific dimerization of methacrolein takes place through a very asynchronous and symmetrical transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The geometrical features of the transition structures correspond well to a case of diradical formation. A cage of secondary orbital interactions restricts the flexibility of the diradical transition structure and stabilizes it. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5077 / 5080
页数：4
相关论文
共 50 条
  • [21] DIHYDROSELENAPYRANS BY [4+2] CYCLOADDITION OF DIARYL SELENOKETONES
    HOCK, R
    HILLENBRAND, S
    ERKER, G
    KRUGER, C
    WERNER, S
    CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08): : 1895 - 1903
  • [22] UTILIZATION OF VINYLSILANES IN [4+2] CYCLOADDITION REACTIONS
    PADWA, A
    MACDONALD, JG
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19): : 3189 - 3195
  • [23] Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes
    Ni, Dongshun
    Witherspoon, Brittany P.
    Zhang, Hong
    Zhou, Chen
    Houk, K. N.
    Brown, M. Kevin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11432 - 11439
  • [24] [4+2]-Cycloaddition of diethyl allylmalonate to cyclopentadienes
    Mamedov, EG
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 36 (12) : 1732 - 1734
  • [25] [4+2] CYCLOADDITION OF N-SULFINYLCARBOXAMIDES
    CARPANELLI, C
    GAIANI, G
    SANCASSAN, F
    CHIMICA & L INDUSTRIA, 1982, 64 (7-8): : 526 - 526
  • [26] Photoinduced Reductive [4+2] Cycloaddition of Nitroarenes
    Kaneko, Taiki
    Ito, Rin
    Okamura, Toshitaka
    Sato, Takaaki
    ORGANIC LETTERS, 2025, 27 (09) : 2042 - 2048
  • [27] (4+2)CYCLOADDITION REACTION OF METHYL CYCLOPENTADIENECARBOXYLATE
    NALLET, JP
    ARNAUD, C
    HUET, J
    TETRAHEDRON LETTERS, 1979, (28) : 2583 - 2584
  • [28] [4+2] Cycloaddition on densely functionalized cyclopentadiene
    Fusi, Stefania
    Ferrini, Serena
    Ponticelli, Fabio
    TETRAHEDRON LETTERS, 2011, 52 (51) : 6911 - 6915
  • [29] [4+2] and [2+4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
    Bujalska, Anna
    Basran, Kaleena
    Luedtke, Nathan W.
    RSC CHEMICAL BIOLOGY, 2022, 3 (06): : 698 - 701
  • [30] Anionic [4+2] cycloaddition strategy in the regiospecific synthesis of carbazoles: formal synthesis of ellipticine and murrayaquinone A
    Mal, Dipakranjan
    Senapati, Bidyut Kumar
    Pahari, Pallab
    TETRAHEDRON, 2007, 63 (18) : 3768 - 3781
12345