A METHYL-GROUP EFFECT ON THE CONFORMATION OF METHYLATED [3.2]METACYCLOPHAN-10-ENES

被引：32

作者：

GRUTZMACHER, HF

NEUMANN, E

机构：

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 06期

关键词：

3.2]METACYCLOPHAN-10-ENES; MCMURRY REACTION; REDUCTIVE COUPLING;

D O I：

10.1002/cber.19931260635

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The syntheses of 7,13-dimethyl[3.2]metacyclophan-10-ene (5) and 7,10,11,13-tetramethyl[3.2]metacyclophan-10-ene (6) starting from 1,3-bis(4-methylphenyl)propane (1) are reported. 5 exists in the anti conformation typical of [3.2]metacyclophanenes while 6 prefers the syn conformation because of steric repulsion between the methyl groups at the etheno bridge and at the aromatic rings.

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页码：1495 / 1497

页数：3

相关论文

共 19 条

[1] SYNTHESES OF 2.2!METACYCLOPHAN-1-ENES - AN ALTERNATE ROUTE TO TRANS-15,16-DIALKYLDIHYDROPYRENES [J].

BLASCHKE, H ;

RAMEY, CE ;

CALDER, I ;

BOEKELHE.V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) :3675-&

[2] SYN-ANTI-CONFORMERS AND SYN-ANTI-REARRANGEMENTS OF INTRAANULARLY AND EXTRAANULARLY SUBSTITUTED DITHIA[3.3]METACYCLOPHANES [J].

BOCKMANN, K ;

VOGTLE, F .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (03) :1065-1073

[3] (3.3)METACYCLOPHANES WITH ANTI CONFORMATION [J].

BREITENBACH, J ;

HOSS, R ;

NIEGER, M ;

RISSANEN, K ;

VOGTLE, F .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (01) :255-258

[4]

EBMEYER F, 1986, THESIS U BIELEFELD

[5] STERIC INTERACTIONS IN ORGANIC-CHEMISTRY - SPATIAL REQUIREMENTS OF SUBSTITUENTS [J].

FORSTER, H ;

VOGTLE, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (07) :429-441

[6]

Forster H., 1977, ANGEW CHEM, V89, P443

[7] [O-9,O-24][2.1.2.1]METACYCLOPHANE-9-ENE, A TWIN CYCLOPHANE, AND ITS DEHYDROGENATION PRODUCTS - SYNTHESIS, STRUCTURE DETERMINATION AND H-1 NMR-SPECTROSCOPY [J].

GRUTZMACHER, HF ;

HUSEMANN, W .

TETRAHEDRON LETTERS, 1985, 26 (20) :2431-2434

[8] [3.2]PARACYCLOPHANE-10-ENES AND [3.2.3.2]PARACYCLOPHANE-10,27-DIENES - A CONVENIENT SYNTHESIS BY THE MCMURRY REACTION AND DYNAMIC STEREOCHEMISTRY [J].

GRUTZMACHER, HF ;

NEUMANN, E ;

EBMEYER, F ;

ALBRECHT, K ;

SCHELENZ, P .

CHEMISCHE BERICHTE, 1989, 122 (12) :2291-2297

[9] FLEXIBLE MOLECULES WITH DEFINED SHAPE - CONFORMATIONAL DESIGN [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) :1124-1134

[10]

Hoffmann RW, 1992, ANGEW CHEM, V104, P1147, DOI 10.1002/ange.19921040905