On the Question of Stepwise [4+2] Cycloaddition Reactions and Their Stereochemical Aspects

被引:27
|
作者
Jasinski, Radomir [1 ]
机构
[1] Cracow Univ Technol, Dept Organ Chem & Technol, Warszawska 24, PL-31155 Krakow, Poland
来源
SYMMETRY-BASEL | 2021年 / 13卷 / 10期
关键词
Diels-Alder reaction; 4+2] cycloaddition; mechanism; zwitterionic intermediates; biradicals; DIELS-ALDER REACTION; THEORETICAL-ANALYSIS; MOLECULAR-MECHANISM; CYCLOPENTADIENE; BUTADIENE; ETHYLENE; NITROALKENES; 2-BROMO-2-NITROETHENYLPHOSPHONATE; DERIVATIVES; KINETICS;
D O I
10.3390/sym13101911
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Even at the end of the twentieth century, the view of the one-step [4+2] cycloaddition (Diels-Alder) reaction mechanism was widely accepted as the only possible one, regardless of the nature of the reaction components. Much has changed in the way these reactions are perceived since then. In particular, multi-step mechanisms with zwitterionic or diradical intermediates have been proposed for a number of processes. This review provided a critical analysis of such cases.
引用
收藏
页数:17
相关论文
共 50 条
  • [12] Asymmetric [4+2] cycloaddition reactions of N-sulfinylcarbamates.
    Whitesell, JK
    Zhang, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 209 - ORGN
  • [13] [4+2] dimerization and cycloaddition reactions of α,β-unsaturated selenoaldehydes and selenoketones
    Li, GM
    Niu, SQ
    Segi, M
    Zingaro, RA
    Yamamoto, H
    Watanabe, K
    Nakajima, T
    Hall, MB
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1565 - 1575
  • [14] SACCHAROMYCES-CEREVISIAE IN THE CATALYSIS OF [4+2] CYCLOADDITION REACTIONS
    RAO, KR
    BHANUMATHI, N
    NAGESWAR, YVD
    SRINIVASAN, TN
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (12): : 937 - 938
  • [15] REACTIONS OF DIAZENEDIYL COMPOUNDS WITH PYRIDONES - NOVEL [4+2] CYCLOADDITION
    KANE, VV
    WERBLOOD, H
    LEVINE, SD
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (03) : 673 - 674
  • [16] [4+2]-cycloaddition reactions involving α-oxo thioketone intermediates
    Hegab, MI
    Abd El-Galil, AA
    Abdel-Megeid, FME
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2002, 57 (08): : 922 - 927
  • [17] CARBOHYDRATES AS CHIRAL TEMPLATES IN STEREOSELECTIVE [4+2] CYCLOADDITION REACTIONS
    KUNZ, H
    MULLER, B
    PFRENGLE, W
    RUCK, K
    STAHLE, W
    ACS SYMPOSIUM SERIES, 1992, 494 : 130 - 146
  • [18] Functionalizing a carbon sphere by way of [4+2]-cycloaddition reactions
    Krautler, B
    PROCEEDINGS OF THE SYMPOSIUM ON RECENT ADVANCES IN THE CHEMISTRY AND PHYSICS OF FULLERENES AND RELATED MATERIALS, VOL 3, 1996, 96 (10): : 1284 - 1294
  • [19] Local softness as a regioselectivity indicator in [4+2] cycloaddition reactions
    Damoun, S
    VandeWoude, G
    Mendez, F
    Geerlings, P
    JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (05): : 886 - 893
  • [20] A mild alternative to the use of benzyne in [4+2]cycloaddition reactions
    Cossu, S
    DeLucchi, O
    TETRAHEDRON, 1996, 52 (45) : 14247 - 14252