The Sensitized Photooxidation of Cycloheptatriene (Tropilidene). Isolation and Thermal Isomerization of (4π+2π) Cycloadduct, 8,9-Dioxabicyclo[3.2.2]-2,6-nonadiene, and Preparation of Tropone

The sensitized photooxidation of cycloheptatriene (tropilidene) in methanol afforded (4π+2π) cycloadduct; 8,9-dioxabicyclo[3.2.2]-2,6-nonadiene (1), 6-hydroxy-2,4-cycloheptadienone and 6-oxoheptadienal presumably derived from (6π+2π) cycloadduct, and small amounts of tropone and benzaldehyde. Mechan...

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Published inBulletin of the Chemical Society of Japan Vol. 51; no. 7; pp. 2131 - 2135
Main Authors Asao, Toyonobu, Yagihara, Morio, Kitahara, Yoshio
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.07.1978
Chemical Society of Japan
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Summary:The sensitized photooxidation of cycloheptatriene (tropilidene) in methanol afforded (4π+2π) cycloadduct; 8,9-dioxabicyclo[3.2.2]-2,6-nonadiene (1), 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 1 in refluxing xylene afforded cis-3,9-dioxatricyclo-[6.1.0.02.4]-5-nonene, 8-oxabicyclo[5.1.0]-4-octen-3-one and 4-hydroxy-2,6-cycloheptadienone.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.51.2131