Conformational Flexibility of Fused Tetracenedione Propellers Obtained from One-Pot Reductive Dimerization of Acetylenic Quinones

Reductive dimerization of acetylenic anthraquinones provides synthetic access to flexible nonplanar polyaromatics with a tetracenedione core. In solution, these nonplanar, contorted polycycles exist as equilibrating mixtures of two symmetric conformers. The fused tetracenediones are easily reduced a...

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Published inJournal of organic chemistry Vol. 80; no. 3; pp. 1618 - 1631
Main Authors Vasilevsky, Sergei F, Baranov, Denis S, Mamatyuk, Victor I, Fadeev, Dmitry S, Gatilov, Yurii V, Stepanov, Aleksandr A, Vasilieva, Nadezhda V, Alabugin, Igor V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.02.2015
Amer Chemical Soc
Subjects
anthraquinones
Chemistry
Chemistry, Organic
dimerization
electrochemistry
organic chemistry
Physical Sciences
Science & Technology
CASCADE TRANSFORMATIONS
RADICAL CASCADES
CARBON
CYCLIZATIONS
2-ELECTRON TRANSFERS
ALKYNES
ONE-ELECTRON
DERIVATIVES
OXOISOAPORPHINE ALKALOIDS
RING-CLOSURE
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Summary:Reductive dimerization of acetylenic anthraquinones provides synthetic access to flexible nonplanar polyaromatics with a tetracenedione core. In solution, these nonplanar, contorted polycycles exist as equilibrating mixtures of two symmetric conformers. The fused tetracenediones are easily reduced and exhibit rich electrochemical behavior.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo502543b