Thermally induced cyclobutenone rearrangements and domino reactions

被引：36
|
作者：
Harrowven, David C. [1 ]
Pascoe, David D. [1 ]
Guy, Ian L. [1 ]
机构：
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期
基金：
英国工程与自然科学研究理事会;
关键词：
cyclization; domino reactions; rearrangement; spiro compounds; thermochemistry;
D O I：
10.1002/anie.200603538
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：425 / 428
页数：4
相关论文
共 50 条
  • [21] Asymmetric organocatalytic domino reactions of γ-nitroketones and enals
    Enders, Dieter
    Narine, Arun A.
    Benninghaus, Thomas R.
    Raabe, Gerhard
    SYNLETT, 2007, (11) : 1667 - 1670
  • [22] Recent Developments on Domino Metathesis Reactions in India
    Nandurdikar, Rahul S.
    Kaliappan, Krishna P.
    CHIMIA, 2012, 66 (12) : 899 - 904
  • [23] Domino Reactions of Tertiary Enamides in Organic Synthesis
    Tong, Shuo
    Wang, Mei-Xiang
    SYNLETT, 2021, 32 (14) : 1419 - 1427
  • [24] Development of Domino Reactions Based on Skeletal Rearrangement
    Sugimoto, Kenji
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2011, 131 (11): : 1563 - 1573
  • [25] Domino reactions of chromones with activated carbonyl compounds
    Langer, Peter
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1256 - 1269
  • [26] Recent Developments in Asymmetric Organocatalytic Domino Reactions
    Pellissier, Helene
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) : 237 - 294
  • [27] The Development of Domino Reactions Incorporating the Heck Reaction: The Formation of N-Heterocycles
    Rixson, James E.
    Chaloner, Thomas
    Heath, Charles H.
    Tietze, Lutz F.
    Stewart, Scott G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (03) : 544 - 558
  • [28] Rearrangements in the course of nucleophilic substitution reactions
    Dax, K
    Albert, M
    GLYOSCIENCE: EPIMERISATION, ISOMERISATION AND REARRANGEMENT REACTIONS OF CARBOHYDRATES, 2001, 215 : 193 - 275
  • [29] Domino Michael aldol and domino Michael Mannich reactions: highly stereoselective synthesis of functionalized cyclohexanes
    Schneider, C
    Reese, O
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (16) : 2948 - 2950
  • [30] Copper-Catalyzed Domino Homologation and Cycloisomerization Reactions for 3-Pyrroline Synthesis
    Shin, Ye Ho
    Maheswara, Muchchintala
    Hwang, Joon Young
    Kang, Eun Joo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (11) : 2305 - 2311
12345