Synthesis and reaction of 1,4-acetal-bridged 2,3,5,6-tetramethylidene-bicyclo[2.2.0]hexane: the first Diels-Alder route to Dewar benzenes

被引：1
|
作者：
Ohkita, M [1 ]
Suzuki, T [1 ]
Tsuji, T [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
来源：
CHEMICAL COMMUNICATIONS | 1999年 / 19期
关键词：
D O I：
10.1039/a906239d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 1,4-acetal-bridged derivative of hitherto unknown 2,3,5,6-tetramethylidenebicyclo[2.2.0]hexane, which produces the Dewar benzene skeleton through two successive Diels-Alder reactions with dienophiles, has been synthesized in four steps from dimethyl acetylenedicarboxylate and 1,4-dichlorobut-2-ene.
引用
收藏
页码：1999 / 2000
页数：2
相关论文
共 29 条
  • [1] A 2,3,5,6-tetramethylenebicyclo[2.2.0]hexane derivative: a novel bisdiene molecule that produces a Dewar benzene skeleton upon two successive Diels-Alder reactions with dienophiles
    Ohkita, M
    Sano, K
    Dohba, S
    Fujita, Y
    Suzuki, T
    Tsuji, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12): : 1971 - 1975
  • [2] ANTHRACYCLINONES .2. SYNTHESIS OF (+/-)-4-DEMETHOXYDAUNOMYCINONE BY DOUBLE DIELS-ALDER ADDITIONS TO 2,3,5,6-TETRAMETHYLIDENE-7-OXANORBORNANE
    BESSIERE, Y
    VOGEL, P
    HELVETICA CHIMICA ACTA, 1980, 63 (01) : 232 - 243
  • [3] THE EFFECT OF PRESSURE ON THE TRIMERIZATION AND DIELS-ALDER REACTION OF CYANOACETYLENE - SYNTHESIS AND REACTIVITY OF 2,3,5-TRICYANOBICYCLO[2.2.0]HEXA-2,5-DIENE (TRICYANO DEWAR BENZENE)
    BREITKOPF, V
    HOPF, H
    KLARNER, FG
    WITULSKI, B
    ZIMNY, B
    LIEBIGS ANNALEN, 1995, (04): : 613 - 617
  • [4] Preparation of polyimides utilizing the Diels-Alder reaction. 1,4-[N,N'-Bis(butadienyl-2-methyl)diamido]-2,3,5,6-tetramethylbenzenes with bismaleimides
    Smith, JG
    Sun, F
    Ottenbrite, RM
    MACROMOLECULES, 1996, 29 (04) : 1123 - 1130
  • [5] INTERACTION BETWEEN NON-CONJUGATED CHROMOPHORES .22. SYNTHESIS AND DIELS-ALDER REACTIVITY OF 1-(DIMETHOXY)METHYL-2,3,5,6-TETRAMETHYLIDENE-7-OXABICYCLO[2.2.1]HEPTANE
    METRAL, JL
    VOGEL, P
    HELVETICA CHIMICA ACTA, 1985, 68 (02) : 334 - 337
  • [6] First example of Diels-Alder reaction in the 2,3,4,4a-tetrahydroquinoline series. Synthesis of hydrogenated 5,8-ethanoquinolines
    Nikitina, Eugeniya V.
    Khrustalev, Victor N.
    Grudinin, Dmitry G.
    Toze, Flavien A. A.
    Kouznetsov, Vladimir V.
    Zubkov, Fedor I.
    TETRAHEDRON, 2010, 66 (15) : 2889 - 2894
  • [7] A direct route to 6,6′-disubstituted-2,2′-bipyridines by double Diels-Alder/retro Diels-Alder reaction of 5,5′-bi-1,2,4-triazines.: Part 29.: 1,2,4-triazines in organic synthesis
    Branowska, D
    MOLECULES, 2005, 10 (01) : 274 - 278
  • [8] Synthesis and study of reactivity in the Diels-Alder reaction of 3-methoxycarbonylindeno[1,2-6]pyran-2(5H)-ones
    Moglioni, AG
    Martinez, AR
    Sosnik, AD
    Iglesias, GYM
    JOURNAL OF CHEMICAL RESEARCH-S, 1996, (11): : 500 - 501
  • [9] Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles
    Fujita, R
    Yoshisuji, T
    Wakayanagi, S
    Wakamatsu, H
    Matsuzaki, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (02) : 204 - 208
  • [10] Exploring the Reactivity of (E)-3(5)-(2-Hydroxyphenyl)-5(3)-styryl-1H-pyrazoles as Dienes in the Diels-Alder Reaction: A New Synthesis of 1H-Indazoles
    Cardoso, Ines C. S.
    Silva, Vera L. M.
    Silva, Artur M. S.
    SYNLETT, 2015, 26 (07) : 945 - 949
123