SYNTHESIS OF ALKYL-SUBSTITUTED AND ALKOXY-SUBSTITUTED BENZILS AND OXIDATIVE COUPLING TO TETRAALKOXYPHENANTHRENE-9,10-DIONES

被引：84

作者：

MOHR, B ^{[1
]}

ENKELMANN, V ^{[1
]}

WEGNER, G ^{[1
]}

机构：

[1] MAX PLANCK INST POLYMER FORSCH,D-55021 MAINZ,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 03期

关键词：

D O I：

10.1021/jo00082a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular Friedel-Crafts acylation of various substituted alkyl- or alkoxybenzenes with oxalyl chloride using carbon disulfide as solvent gave rise to the benzils 1a-k. Subsequent intramolecular oxidative coupling with either thallium(III) oxide/trifluoroacetic acid or vanadium(V) oxyfluoride/boron trifluoride diethyl etherate resulted in the corresponding phenanthrene-9,10-diones 2a-d. It has been shown that oxygen functionalities at the 3, 3', 4, and 4' positions are necessary for coupling to occur. These substituted benzils and phenanthrene-9,10-diones constitute precursors for ligands in the field of discotic metallomesogens or polymeric mesogens.

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页码：635 / 638

页数：4

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