Reactions of spiro[2.6]nona-4,6,8-triene derivatives with acids and bases. Rearrangement to a heptafulvene derivative and formation of ether linkage compounds.
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概要
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Reaction of dimethyl <I>trans</I>-spiro[2.6]nona-4,6,8-trien-1,2-dicarboxylate with phenyllithium afforded <I>trans</I>-1,2-bis(hydroxydiphenylmethyl)spiro[2.6]nona-4,6,8-triene (<B>2</B>) in a good yield. Spirotriene <B>2</B> is very sensitive to acids and gave 8-(2,2-diphenylvinyl) heptafulvene accompanied with a quantitative amount of benzophenone by acid treatments. Although <B>2</B> is stable to basic reagents, upon treating with sodium hydride, <B>2</B> afforded 11-hydroxydiphenylmethyl-8-oxa-9-diphenyltricyclo[5.4.0.0<SUP>1,10</SUP>]undeca-2,4-diene, and its double bond isomers. Mechanisms of the above reactions are discussed.
- 公益社団法人 日本化学会の論文
著者
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Toda Takashi
Department Of Applied Chemistry Faculty Of Engineering Utsunomiya University
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Saito Katsuhiro
Department Of Agricultural And Resource Economics The University Of Tokyo
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Mukai Toshio
Department of Chemistry, Faculty of Science, Tohoku University
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Mukai Toshio
Department of Chemistry, Faculty of Science Tohoku University
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