The thermal cycloaddition of dispiro[2.2.2.2]deca-4,9-diene to isolated carbon-carbon multiple bonds.

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概要

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• The cycloadditions of dispiro[2.2.2.2]deca-4,9-diene (<B>1</B>) to isolated carbon-carbon multiple bonds have proceeded in two different modes, giving dispiro[2.2.4.2]dodeca-4,11-diene and tricyclo[6.4.0.0<SUP>3,6</SUP>]dodeca-2,7-diene derivatives. Mono- and 1,2-disubstituted olefins and acetylenes gave the former adducts, whereas 1,1-disubstituted olefins gave the latter, as the major products. Evidence for the intermediacy of biradicals is provided. The observed difference in the mode of the cycloaddition is explained in terms of the stereoelectronic and/or steric effects in the transition state for the cyclization of the intermediate. The addition of <B>1</B> to tetracyanoethylene (TCNE) in wet acetone has proceeded <I>via</I> a zwitterionic intermediate(s), giving a 1:1:1 adduct of <B>1</B>, TCNE, and water.

• 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

• Nishida Shinya

  Department of Chemistry, Faculty of Engineering Science, Osaka University

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