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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Abstract 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.
AbstractList 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.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.
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.
Author Baranov, Denis S
Gatilov, Yurii V
Vasilieva, Nadezhda V
Vasilevsky, Sergei F
Alabugin, Igor V
Fadeev, Dmitry S
Mamatyuk, Victor I
Stepanov, Aleksandr A
AuthorAffiliation N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Department of Chemistry and Biochemistry
Siberian Branch of the Russian Academy of Sciences
Florida State University
Institute of Chemical Kinetics and Combustion
Novosibirsk State University
AuthorAffiliation_xml – name: Novosibirsk State University
– name: N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
– name: Florida State University
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Issue 3
Keywords CASCADE TRANSFORMATIONS
RADICAL CASCADES
CARBON
CYCLIZATIONS
2-ELECTRON TRANSFERS
ALKYNES
ONE-ELECTRON
DERIVATIVES
OXOISOAPORPHINE ALKALOIDS
RING-CLOSURE
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Snippet Reductive dimerization of acetylenic anthraquinones provides synthetic access to flexible nonplanar polyaromatics with a tetracenedione core. In solution,...
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SubjectTerms anthraquinones
Chemistry
Chemistry, Organic
dimerization
electrochemistry
organic chemistry
Physical Sciences
Science & Technology
Title Conformational Flexibility of Fused Tetracenedione Propellers Obtained from One-Pot Reductive Dimerization of Acetylenic Quinones
URI http://dx.doi.org/10.1021/jo502543b
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https://www.ncbi.nlm.nih.gov/pubmed/25575160
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