Antiaromatic Dianions: Dianions of Dixanthyiidene by Reduction and Attempted Excited-State Deprotonation

被引：6

作者：

Black, Mary ^{[1
]}

Woodford, Clifford ^{[1
]}

Mills, Nancy S. ^{[1
]}

机构：

[1] Trinity Univ, Dept Chem, San Antonio, TX 78212 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

基金：

美国国家科学基金会;

关键词：

INDEPENDENT CHEMICAL-SHIFTS; CYCLIC VOLTAMMETRY; AROMATICITY INDEX; FLUORENYL CATIONS; DICATIONS; PARATROPICITY/ANTIAROMATICITY; CARBANIONS; GENERATION; ANION;

D O I：

10.1021/jo102449y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of dixanthylidene with potassium or lithium resulted in formation of the c.ntiaromatic dianion in high yield. Attempts to form the dianion by excited-state deprotonation of dixanthene with n-butyllithium/TMEDA resulted in formation of the tetraanion from deprotonation ortho to the oxygen. Orientation of the sp(3) hydrogens presumably allows preferential deprotonation of the xanthene rings.

引用

页码：2286 / 2290

页数：5

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