SYNTHESIS AND STRUCTURE OF 1,10-ORTHO-BENZENO[2.2]ORTHOCYCLOPHANE-5,6,12,15-DIQUINONE - AN EXPERIMENTAL-EVIDENCE FOR ATTRACTIVE INTERACTION BETWEEN ORTHO-BENZOQUINONE AND PARA-BENZOQUINONE

被引:6
作者
FUKAZAWA, Y
NAKAMURA, T
USUI, S
机构
[1] Department of Chemistry, Faculty of Science, Hiroshima University, Hiroshima
关键词
D O I
10.1016/S0040-4039(00)79717-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound (2) was synthesized by cycloaddition of 4,5-dimethoxybenzocyclobutene and 1,4-diacetoxyanthracene and subsequent hydrolysis followed by oxidations. The syn conformer of 2 was proven to be more stable than anti implying that through space interaction between o- and p-benzoquinone is attractive.
引用
收藏
页码:3183 / 3186
页数:4
相关论文
共 21 条
[1]   BENZENE, AROMATIC RINGS, VANDERWAALS MOLECULES, AND CRYSTALS OF AROMATIC-MOLECULES IN MOLECULAR MECHANICS (MM3) [J].
ALLINGER, NL ;
LII, JH .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (08) :1146-1153
[2]   THEORETICAL INTERPRETATION OF THE ABSORPTION AND IONIZATION SPECTRA OF THE PARACYCLOPHANES [J].
CANUTO, S ;
ZERNER, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2114-2120
[3]   MACRO RINGS .31. QUINONE DERIVED FROM [2.2]PARACYCLOPHANE AN INTRAMOLECULAR-MOLECULAR COMPLEX [J].
CRAM, DJ ;
DAY, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) :1227-&
[4]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[5]   SPIROCONJUGATION [J].
DURR, H ;
GLEITER, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (08) :559-569
[6]   SYNTHESIS AND STRUCTURE OF 1,11-ORTHO-BENZENO[2]ORTHOCYCLO[2](4,5)TROPOLONOPHANE [J].
FUKAZAWA, Y ;
OKAJIMA, T ;
USUI, S .
TETRAHEDRON LETTERS, 1990, 31 (09) :1309-1312
[7]   SYNTHESIS AND STRUCTURE OF 1,11-ORTHO-BENZENO[2]ORTHOCYCLO[2](4,5)TROPONOPHANES [J].
FUKAZAWA, Y ;
OKAJIMA, T ;
FUJIHARA, T ;
USUI, S .
TETRAHEDRON LETTERS, 1988, 29 (46) :5961-5964
[8]   THE PHOTOCHEMICAL-REACTION OF 9-CYANOANTHRACENE WITH S-CISOID 2,3-DISUBSTITUTED BUTADIENES AND THE MOLECULAR-STRUCTURES OF THEIR PHOTOCHEMICAL [4+4]ADDUCTS [J].
FUKAZAWA, Y ;
FUJIHARA, T ;
USUI, S ;
SHIOBARA, Y ;
KODAMA, M .
TETRAHEDRON LETTERS, 1986, 27 (46) :5621-5624
[9]   1,11-ORTHO-BENZENO[2]ORTHOCYCLO[1](6,8)HEPTAFULVENOPHANE A NEW ROUTE TO HEPTAFULVENE FROM 8,8-DICHLORO-3-ALKYL-4-OXATRICYCLO[5,1,0,03,5]OCTANE [J].
FUKAZAWA, Y ;
OKAJIMA, T ;
USUI, S .
TETRAHEDRON LETTERS, 1989, 30 (24) :3163-3166
[10]   INTERACTIONS BETWEEN NONCONJUGATED PI-SYSTEMS [J].
GLEITER, R ;
SCHAFER, W .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (11) :369-375