The present investigation was undertaken in order to see whether singlet oxygen-oxidation of unconjugated cyclic dienes having spatially close double bonds causes a particular transannular reaction as previously observed with 1,5-cyclooctadiene which gave 4-hydroxy-5-cyclooctenone. Most cyclic dienes tested underwent normal “ene” reaction to give allylic hydroperoxides. Thus, on dye-sensitized photooxygenation
进行本研究是为了观察具有空间上紧密双键的非共轭环状二烯的单线态氧氧化是否会引起特定的跨环反应,如先前观察到的
1,5-环辛二烯,产生
4-羟基-5-环
辛烯。大多数测试的环二烯经历了正常的“烯”反应以产生烯
丙基氢过氧化物。因此,在
染料敏化光氧化,然后用
亚硫酸盐、双
环戊二烯、顺式、反式-1,5-环癸二烯、反式、反式、反式 1,5,9-
环辛二烯、1,4-
环辛二烯、1,3-
环辛二烯和基马克隆还原产生
三环[5.2.1.02,6]癸烷-4,8-二烯-3-醇、顺,顺-2,7-环癸二烯醇的立体异构混合物,两种2,5,9-环十二碳
三烯醇的立体异构混合物,2, 4-
环辛二烯醇、环
辛烯的内-3,8-过氧化物和germacra-3,7(11),分别为 10(14)-trien-9-ol-6-one(E)。在类似条件下,降
冰片二烯和顺,顺-
1,6-环癸二烯几乎保持不变。