The sensitized photooxidation of cycloheptatriene (tropilidene). Isolation and thermal isomerization of (4.PI.+2.PI.) cycloadduct, 8,9-dioxabicyclo-[3.2.2]-2,6-nonadiene, and preparation of tropone.

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概要

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• The sensitized photooxidation of cycloheptatriene (tropilidene) in methanol afforded (4π+2π) cycloadduct; 8,9-dioxabicyclo[3.2.2]-2,6-nonadiene (<B>1</B>), 6-hydroxy-2,4-cycloheptadienone and 6-oxoheptadienal presumably derived from (6π+2π) cycloadduct, and small amounts of tropone and benzaldehyde. Mechanism of their formation are discussed. It was found that the treatment of the photooxidation mixture with trie thy lamine afforded tropone in about 50% yield. Thermal isomerization of <B>1</B> in refluxing xylene afforded <I>cis</I>-3,9-dioxatricyclo-[6.1.0.0<SUP>2.4</SUP>]-5-nonene, 8-oxabicyclo[5.1.0]-4-octen-3-one and 4-hydroxy-2,6-cycloheptadienone.

• 公益社団法人 日本化学会の論文

著者

• Kitahara Yoshio

  Department Of Chemistry Faculty Of Science Tohoku University

• Asao Toyonobu

  Department of Chemistry Faculty of Science Tohoku University

• Yagihara Morio

  Department of Chemistry, Faculty of Science, Tohoku University

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