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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (8): 791-795. 上一篇    下一篇

研究论文

顺, 顺-1,5-环辛二烯的单重态氧反应及其产物的重排

陈东立;何慧珠;李琼瑶;萧绪玲;王夺元   

  1. 中国科学院感光化学研究所
  • 发布日期:1988-08-15

Singlet oxygenation of cis, cis-1,5-cyclooctadiene and thermal rearrangement of product

CHEN DONGLI;HE HUIZHU;LI QIONGYAO;XIAO XULING;WANG DUOYUAN   

  • Published:1988-08-15

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本文报道用竹红菌甲素作光敏剂匹配高压钠灯光源, 对1,5-环辛二烯(1)进行单重态氧氧化反应, 高产率和立体选择性地得到顺-5,8-二(氢过氧基)-1,3-环辛二烯(7). 证明了7还原产物顺-5,8-二烃基-1,3-环辛二烯(8)热重排的产物是6-羟基-4-环辛烯酮(3). 而不是6-羟基-3-环辛烯酮(6). 并讨论了热重排过程的机理.

关键词: 重排反应, 过氧化氢 P, 立体选择性, 钠灯, 跨环反应, 单线态氧, 光敏化剂, 环辛二烯 P, 环辛二烯 P, 烯酮

With hypocrellin A associated high pressure sodium lamp sensitized photooxygenation of cis,cis-1,5-cyclooctadiene in methanol gave cis-5,8-dihydroperoxyl-1,3-cyclooctadiene efficiently and stereoselectively. It is shown that cis-5,8-dihydroxy-1,3-cyclooctadiene is thermally rearranged to 6-hydroxy-4-cyclooctenone instead of 6-hydroxy-3-cyclooctenone. The thermal rearrangement process was discussed.

Key words: REARRANGEMENT REACTION, HYDROPEROXIDE P, STEREOSELECTIVITY, SODIUM LAMPS, PERICYCLIZATION, SINGLET OXYGEN, PHOTOSENSITIZER, CYCLOOCTADIENE P, CYCLOOCTADIENE P, KETENE

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