Poly-Oxygenated Tricyclobutabenzenes via Repeated [2 + 2] Cycloaddition of Benzyne and Ketene Silyl Acetal

Described herein is a synthesis of highly functionalized tricyclobutabenzenes, a class of molecules of structural and theoretical interest. The preparation is based on the repeated [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where two types of regioselectivity enable discrimin...

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Published inJournal of the American Chemical Society Vol. 128; no. 11; pp. 3534 - 3535
Main Authors Hamura, Toshiyuki, Ibusuki, Yousuke, Uekusa, Hidehiro, Matsumoto, Takashi, Suzuki, Keisuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.03.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CYCLOHEXATRIENE
TRIS(BENZOCYCLOBUTADIENO)BENZENE
RINGS
BOND LENGTHS
ALPHA-ALKOXYBENZYNE
CRYSTAL-STRUCTURES
PI
LONE-PAIR REPULSIONS
BENZENES
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Summary:Described herein is a synthesis of highly functionalized tricyclobutabenzenes, a class of molecules of structural and theoretical interest. The preparation is based on the repeated [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where two types of regioselectivity enable discrimination of the functionalities on the four-membered rings. By these steps, we were able to prepare poly-oxygenated octamethoxytricyclobutabenzene and its hydrolyzed tetra-oxo derivatives. Structural study on the latter compound showed the interesting properties related to the strained four-membered ring.
Bibliography:ark:/67375/TPS-8DWVD5PW-5
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja0602647