Stereospecific [2π+2π+2π] Cycloaddition Reaction of Norbornadiene

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概要

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• [2π+2π+2π] cycloaddition reaction of <I>cis</I>- or <I>trans</I>-disubstituted olefinic dienophiles (<B>4a</B>–<B>4e</B>) to bicyclo[2.2.1]hepta-2,5-diene (<B>1</B>, norbornadiene) was found to be stereospecific. The cycloadducts obtained, 4,5-disubstituted tetracyclo[4.2.1.0.<SUP>2,9</SUP>0<SUP>3,7</SUP>]nonane (<B>5,6</B>) conserved the original stereochemistry in the dienophiles, strongly suggesting the presence of <I>homo</I>-conjugation in <B>1</B>. A striking contrast between cycloaddition reaction of quadricyclane (a valence bond isomer of <B>1</B>) and that of norbornadiene was understood by application of the principle of orbital symmetry conservation to these cycloadditions.

• 公益社団法人 日本化学会の論文

著者

• Togashi Atsushi

  Department Of Computer Science Shizuoka University

• Yoshida Zen-ichi

  Department Of Applied Chemistry Faculty Of Science And Engineering Kinki University

• Tabushi Iwao

  Faculty of Pharmaceutical Sciences, Kyushu University

• Yamamura Kazuo

  Faculty of Pharmaceutical Sciences, Kyushu University

• Yoshida Zen-ichi

  Department of Synthetic Chemistry, Kyoto University

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