STRUCTURES OF STERICALLY OVERCROWDED OR CHARGE-PERTURBED MOLECULES .8. STRUCTURAL-CHANGES ON TWOFOLD OXIDATION OF TETRAKIS(DIMETHYLAMINO)-PARA-BENZOQUINONE - A STERICALLY OVERCROWDED ELECTRON-RICH CHAIR COMPOUND TURNS INTO A TWIST DICYANINE SALT

被引:31
作者
BOCK, H
RUPPERT, K
NATHER, C
HAVLAS, Z
机构
[1] Institut für Anorganische Chemie, Universität Frankfurt, Frankfurt am Main, W-6000, Niederurseler Hang
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 09期
关键词
D O I
10.1002/anie.199111801
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
On account of the four bulky (H3C)2N-substituents the tetrakis(dimethylamino)-p-benzoquinone molecule is electron-rich and sterically overcrowded. It has a chair conformation in which the O = C groups are bent 12-degrees above and below the central C4 plane. Oxidation with SbCl5/CH2Cl2 leads to a dication-bis(hexachloroantimonate), which is distorted to a twist conformation with dihedral angles of 35-degrees by formation of two cyanine chains R2NC-C(O)-CNR2+; at the same time the quinone C = C bonds are stretched from 137 to 146 pm (see structure on the right). [GRAPHICS]
引用
收藏
页码:1180 / 1183
页数:4
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