Thermodynamically Stable o-Quinodimethane: Synthesis, Structure, and Reactivity

被引：6
|
作者：
Adachi, Kazuhiko [1 ]
Hirose, Shunsuke [1 ]
Ueda, Yasuyuki [1 ]
Uekusa, Hidehiro [2 ]
Hamura, Toshiyuki [1 ]
机构：
[1] Kwansei Gakuin Univ, Dept Appl Chem Environm, 2-1 Gakuen, Sanda 6691337, Japan
[2] Tokyo Inst Technol, Sch Sci, Dept Chem, Meguro Ku, Ookayama 2, Tokyo 1528551, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 11期
关键词：
aryne; cycloaddition; cyclobutaarenes; polycyclic aromatic hydrocarbon; quinodimethanes; CONROTATORY ELECTROCYCLIC REACTIONS; CARBON-CARBON; RING OPENINGS; PRECURSOR; ARYNE; 7,7,8,8-TETRAARYL-O-QUINODIMETHANE; STEREOSELECTIVITIES; CYCLOBUTENES; BENZYNE; SYSTEM;
D O I：
10.1002/chem.202004510
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Thermal isomerization of cyclobutaphenanthrene to o-quinodimethane was investigated. Sterically congested substituents or electron-donating substituents on the four-membered ring promoted the ring-opening, affording o-quinodimethane in a relatively stable form. Isolation of the newly prepared o-quinodimethane allowed its structural elucidation and investigation of its potential reactivities. Dual [4+2] cycloaddition of an aryne and o-quinodimethane afforded tetrabenzopentacene, demonstrating the synthetic application of the isolated compound.
引用
收藏
页码：3665 / 3669
页数：5
相关论文
共 50 条
  • [41] Functionalised pyridine sulfolenes as precursors to pyridine o-quinodimethane derivatives and their [4+2] cycloadducts
    Cappelle, SL
    Vogels, IA
    Van Meervelt, L
    Compernolle, F
    Hoornaert, GJ
    TETRAHEDRON LETTERS, 2001, 42 (22) : 3759 - 3762
  • [42] Stable thioaldehydes and selenoaldehydes: Synthesis, structure and reactivity
    Tokitoh, N
    Okazaki, R
    POLISH JOURNAL OF CHEMISTRY, 1998, 72 (06) : 971 - 1000
  • [43] Synthesis, Structure, and Reactivity of a Thermally Stable Dialkylgermylene
    Suzuki, Fumiaki
    Nishino, Ryohei
    Yukimoto, Mariko
    Sugamata, Koh
    Minoura, Mao
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2020, 93 (02) : 249 - 251
  • [44] Synthesis, structure, and reactivity of a thermally stable dialkylgermylene
    Suzuki, Fumiaki
    Nishino, Ryohei
    Yukimoto, Mariko
    Sugamata, Koh
    Minoura, Mao
    Bulletin of the Chemical Society of Japan, 2020, 93 (02): : 249 - 251
  • [45] FUNCTIONALIZED O-BIS(CHLOROMETHYL)PYRIDINES AS PRECURSORS FOR PYRIDINE O-QUINODIMETHANE ANALOGS AND THEIR [4+2] CYCLOADDUCTS
    CARLY, PR
    COMPERNOLLE, F
    HOORNAERT, GJ
    TETRAHEDRON LETTERS, 1995, 36 (12) : 2113 - 2116
  • [46] HETEROCYCLIC COMPOUNDS RELATED TO O-QUINODIMETHANE - 3-OXO-3H-2-BENZOPYRANS AND THEIR SALTS
    HOLLAND, JM
    JONES, DW
    CHEMISTRY & INDUSTRY, 1968, (17) : 549 - &
  • [47] A NOVEL SYNTHETIC ROUTE TO 1-ARYLTETRALIN LIGNAN LACTONE VIA INTERMOLECULAR CYCLOADDITION WITH O-QUINODIMETHANE
    DAS, KG
    AFZAL, J
    HAZRA, BG
    BHAWAL, BM
    SYNTHETIC COMMUNICATIONS, 1983, 13 (09) : 787 - 796
  • [48] GAS-PHASE DIELS-ALDER REACTION OF THE O-QUINODIMETHANE RADICAL CATION AND NEUTRAL STYRENE
    CHESS, EK
    LIN, PH
    GROSS, ML
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09): : 1522 - 1527
  • [49] Catalytic 1,2-dihydronaphthalene and E-aryl-diene synthesis via CoIII-Carbene radical and o-quinodimethane intermediates
    te Grotenhuis, Colet
    Das, Braja G.
    Kuijpers, Petrus F.
    Hageman, Wouter
    Trouwborst, Mees
    de Bruin, Bas
    CHEMICAL SCIENCE, 2017, 8 (12) : 8221 - 8230
  • [50] 2,4-Bis(methylsulfanyl)pyrimidine o-quinodimethane: a versatile building block for functionalized fused pyrimidines
    Herrera, Antonio
    Martinez-Alvarez, Roberto
    Martin, Nazario
    Chioua, Mourad
    Chioua, Rachid
    Sanchez-Vazquez, Angel
    Molero, Dolores
    Almy, John
    TETRAHEDRON, 2009, 65 (08) : 1697 - 1703
12345