REGIOSPECIFIC SYNTHESIS AND STRUCTURAL STUDY OF SOME TRIFLUOROMETHYL SUBSTITUTED DIBENZOSEMIBULLVALENES

被引：5

作者：

OTOCAN, K

MINTAS, M

KASTNER, F

MANNSCHRECK, A

GOLEN, JA

WILLIARD, PG

机构：

[1] UNIV ZAGREB, DEPT ORGAN CHEM, YU-41000 ZAGREB, CROATIA

[2] UNIV REGENSBURG, INST ORGAN CHEM, W-8400 REGENSBURG, GERMANY

[3] BROWN UNIV, DEPT CHEM, PROVIDENCE, RI 02912 USA

[4] SE MASSACHUSETTS UNIV, DEPT CHEM, N DARTMOUTH, MA 02747 USA

来源：

MONATSHEFTE FUR CHEMIE | 1992年 / 123卷 / 12期

关键词：

DIBENZOBARRELENE; DIBENZOSEMIBULLVALENE; ENANTIOSELECTIVE CHROMATOGRAPHY; TRIFLUOROMETHYLATION; PHOTOCHEMICAL REARRANGEMENT; X-RAY CRYSTAL STRUCTURES;

D O I：

10.1007/BF00808282

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Preparation of the regiospecifically trifluoromethyl substituted dibenzosemibullvalenes 3 and 5 is described. An unequivocal proof of chirality of 3 and 5 was obtained by enrichment of their enantiomers using liquid chromatography on triacetyl- or tribenzoylcellulose. The stereostructure of compounds 3 to 5 was proved by their H-1-NMR spectra and confirmed by X-ray crystallographic analysis. The geometrical data from X-ray structural analyses showed that five-membered rings involved in the skeleton of 3 and 5 adopt flattened envelope conformations. These results indicate also a significant substituent-induced bond length asymmetry in the cyclopropane rings of 3 and 5.

引用

页码：1193 / 1205

页数：13

共 18 条

[1] THE GEOMETRY OF SMALL RINGS .2. A COMPARATIVE GEOMETRICAL STUDY OF HYBRIDIZATION AND CONJUGATION IN CYCLOPROPANE AND THE VINYL GROUP [J].