SYNTHESIS, STRUCTURE, AND PHYSICAL-PROPERTIES OF 1,11-O-BENZENO[2]ORTHOCYCLO[2](1,2)TROPYLIOPHANE

被引：11

作者：

FUKAZAWA, Y

HARADA, S

INAI, A

OKAJIMA, T

机构：

[1] Department of Chemistry, Faculty of Science, Hiroshima University, 724, 1-3-1, Kagamiyama, Higashihiroshima

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)61367-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound (2) has been synthesized, the structure and the physical properties of which are investigated by X-ray, spectroscopic analyses, and MO calculations. There exists charge transfer (CT? interaction between the tropylium ion and the facing phenyl ring. From the pK(R)(+) value of 2, it can be clear that the cation 2 is stabilized by the CT interaction. In spite of the presence of bond weakening sigma-pi orbital mixing, the cation 2 withstands retro[4+4]type bond cleavage, which is quite interesting when compared to a facile cleavage for the congener with anthracene photodimer type structure.

引用

页码：8493 / 8496

页数：4

共 28 条

[1] X-RAY CRYSTALLOGRAPHIC STUDIES ON CYCLOHEPTADITHIOPHENE COMPOUNDS AND SIMILAR SYSTEMS .10. CRYSTAL-STRUCTURE OF DITHIENO[1,2-B-5,4-B']TROPYLIUM TETRAFLUOROBORATE AT 143-K AND 295-K [J].

ANDERSSON, JE .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (JUN) :1349-1354

[2] X-RAY CRYSTALLOGRAPHIC STUDIES ON CYCLOHEPTADITHIOPHENE COMPOUNDS AND SIMILAR SYSTEMS .1. CRYSTAL-STRUCTURE OF DITHIENO [2,1-B-4,5-B']TROPYLIUM PERCHLORATE [J].

AURIVILLIUS, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (06) :681-688

[3] SYNTHESIS OF TROPENIUM (CYCLOHEPTA-TRIENYLIUM) SALTS BY HYDRIDE EXCHANGE [J].

DAUBEN, HJ ;

GADECKI, FA ;

HARMON, KM ;

PEARSON, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (16) :4557-4558

[4]

DAUBEN HJ, 1960, J ORG CHEM, V25, P1442

[5] EFFECTS OF SUBSTITUENTS ON THE LENGTH OF CENTRAL C(SP3)-C(SP3) BOND IN ANTHRACENE PHOTODIMERS AND RELATED MOLECULES [J].

DOUGHERTY, DA ;

CHOI, CS ;

KAUPP, G ;

BUDA, AB ;

RUDZINSKI, JM ;

OSAWA, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (07) :1063-1070

[6] BOND LENGTHENING AND THROUGH-BOND INTERACTIONS IN P,P'-DIBENZENE AND RELATED MOLECULES [J].

DOUGHERTY, DA ;

SCHLEGEL, HB ;

MISLOW, K .

TETRAHEDRON, 1978, 34 (10) :1441-1447

[7] 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

[8] 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 [J].

FUKAZAWA, Y ;

NAKAMURA, T ;

USUI, S .

TETRAHEDRON LETTERS, 1991, 32 (27) :3183-3186

[9] 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

[10] 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

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