Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes

Zethrenes were synthesized by Pd‐catalyzed cyclodimerization of 1‐ethynyl‐8‐iodonaphthalenes. The structure of these cycloadducts was confirmed by X‐ray crystal analysis. The bond lengths and bond alternation in the crystal structures reveal that the central two six‐membered rings of the title compo...

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Published inAngewandte Chemie International Edition Vol. 49; no. 39; pp. 7059 - 7062
Main Authors Wu, Tsun-Cheng, Chen, Chia-Hua, Hibi, Daijiro, Shimizu, Akihiro, Tobe, Yoshito, Wu, Yao-Ting
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 17.09.2010
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
aromaticity
Chemistry
Chemistry, Multidisciplinary
cycloaddition
nickel
palladium
Physical Sciences
Science & Technology
nickel
CONDENSED BENZENOID HYDROCARBONS
NAPHTHALENES
POLYCYCLIC AROMATIC-HYDROCARBONS
alkynes
EFFICIENT SYNTHESIS
PHENANTHRENE
MOLECULES
cycloaddition
X-RAY
palladium
ARYL IODIDES
PALLADIUM-CATALYZED ANNULATION
aromaticity
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Summary:Zethrenes were synthesized by Pd‐catalyzed cyclodimerization of 1‐ethynyl‐8‐iodonaphthalenes. The structure of these cycloadducts was confirmed by X‐ray crystal analysis. The bond lengths and bond alternation in the crystal structures reveal that the central two six‐membered rings of the title compounds lack aromaticity.
Bibliography:Metal-Catalyzed Reactions of Alkynes. Part VI. Part V, see ref. 21. This work was supported by the Landmark Project of National Cheng Kung University and the National Science Council of Taiwan (NSC 98-2113M-006-002-MY3) and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We also thank Prof. S.-L. Wang and P.-L. Chen (National Tsing Hua University, Taiwan) for the X-ray structure analyses. The authors are indebted to Prof. Jay Siegel (University of Zurich, Switzerland) for his useful suggestions.
Grant-in-Aid for Scientific Research
Ministry of Education, Culture, Sports, Science and Technology
National Science Council of Taiwan - No. NSC 98-2113M-006-002-MY3
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ArticleID:ANIE201001929
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This work was supported by the Landmark Project of National Cheng Kung University and the National Science Council of Taiwan (NSC 98‐2113M‐006‐002‐MY3) and a Grant‐in‐Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We also thank Prof. S.‐L. Wang and P.‐L. Chen (National Tsing Hua University, Taiwan) for the X‐ray structure analyses. The authors are indebted to Prof. Jay Siegel (University of Zurich, Switzerland) for his useful suggestions.
Metal‐Catalyzed Reactions of Alkynes. Part VI. Part V, see ref.
21
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001929