An Oxidative Macrobicyclic Ring Opening of a Triptycene to a Highly Functionalized Fluorene Derivative

被引：7

作者：

Baumgaertner, Kevin ^{[1
]}

Rominger, Frank ^{[1
]}

Mastalerz, Michael ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 17期

关键词：

CHARGE-TRANSFER TRANSITION; ORGANIC CAGE; REARRANGEMENT; SUBSTITUENT; PHOTOREARRANGEMENT; IPTYCENES; RESONANCE;

D O I：

10.1021/acs.joc.5b01426

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of hexamethoxytriptycenes with nitric acid leads to an unprecedented oxidative ring opening of the triptycene scaffold, resulting in a new class of fluorene derivatives with a nitroquinone unit. Preliminary investigations of the influence of chain length of alkyl substituents at the triptycene bridgeheads to the reaction have been performed, revealing that exclusively the methyl-substituted hexamethoxytriptycene does not undergo an oxidative ring opening reaction.

引用

页码：8881 / 8886

页数：6

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