The cycloaddition of dispiro[2.2.2.2]deca-4,9-diene with the styrene derivatives. The syntheses and spectral properties of the [4.2]paracyclophane derivatives.

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概要

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• The thermal cycloaddition of dispiro[2.2.2.2]deca-4,9-diene <B>1</B> with the styrene derivatives has afforded [4.2]paracyclophane derivatives, <B>3</B>. A reaction mechanism by way of the biradical intermediates, involving the initial homolytic cleavage of the cyclopropane ring in <B>1</B> followed by the addition to the styrene molecule, is proposed. In the reaction of <B>1</B> with styrene, and methyl α-phenylacrylate, the yields of <B>3</B> were improved with the dilution of the reactants, while in the reaction with <I>trans</I>-stilbene, no appreciable dependence on the reactant concentration was observed. The mass spectra of the substituted [4.2]paracyclophanes show a predominant fragmentation to the substituted <I>p</I>-xylene-α,α′-diyl (or elements thereof) ion radical. [4.2]Paracyclophane exhibited a temperature-dependent NMR spectrum which could be ascribed to the rapid equilibration between two structurally equivalent conformers. Bulky substituents on C-1 and C-2 shifted the equilibrium to one side.

• 公益社団法人 日本化学会の論文

著者

• Tsuji Takashi

  Department Of Biological Science And Technology Faculty Of Industrial Science And Technology Tokyo U

• Shibata Tohru

  Department Of Agricultural Chemistry Faculty Of Agriculture Kyoto University

• TSUJI Takashi

  Department of Chemistry, Faculty of Science, Hokkaido University

• Nishida Shinya

  Department of Chemistry, Faculty of Science, Hokkaido University

• Nishida Shinya

  Department of Chemistry, Faculty of Engineering Science, Osaka University

• Shibata Tohru

  Department of Chemistry, Faculty of Science, Hokkaido University

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