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Issue 7, 1989
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o-Pleiadienequinones. Part 3. Ring enlargement of o-pleiadienequinones with diazoalkanes

Junichi Ikuina,  Kazuo Yoshida,  Hiroshi Tagata,  Shigekazu Kumakura  and  Josuke Tsunetsugu 

Abstract

The reactions of o-pleiadienequinones (1) and (2) with various diazoalkanes are described. In the absence of catalyst pyrazoline derivatives (3) and (4) were obtained. In the presence of Lewis acid catalysts ring-enlarged cyclo-octa[de]naphthalenones (5a), (6), and (7a) were obtained, achieving syntheses of the first known higher analogues of phenalenone. The reaction of the quinone (2) with trimethylsilyldiazomethane gave cyclo-octa[de]naphthalenedione (8). The physical properties of these compounds are described and the mechanism of formation is discussed. The quinone (1) formed 1 : 1 complexes with divalent metal ions.

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Article type: Paper
DOI: 10.1039/P19890001305
Citation: J. Chem. Soc., Perkin Trans. 1, 1989,0, 1305-1310
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    o-Pleiadienequinones. Part 3. Ring enlargement of o-pleiadienequinones with diazoalkanes

    J. Ikuina, K. Yoshida, H. Tagata, S. Kumakura and J. Tsunetsugu, J. Chem. Soc., Perkin Trans. 1, 1989, 0, 1305
    DOI: 10.1039/P19890001305

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