6-甲基-6-乙烯基富烯的一种极其简单高效的合成方法及其氧化转化反应。
An exceptionally simple and efficient synthesis of 6-methyl-6-vinylfulvene, and its oxidative transformations.
作者信息
Erden Ihsan, Gärtner Christian
机构信息
San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
出版信息
Tetrahedron Lett. 2009 May 20;50(20):2381-2383. doi: 10.1016/j.tetlet.2009.02.221.
Abstract
A new efficient synthesis of 6-methyl-6-vinylfulvene was developed, starting from the 6-(2-hydroxyethyl)-6-methylfulvene. With larger quantities of the title compound in hand, its photooxygenation with singlet oxygen was studied. Cyclization of the cyclopropanone intermediate to both vinyl moieties in the unsaturated system was observed, whereas the saturated endoperoxide gave mostly the cyclopentenone derivative. m-CPBA attacks exclusively the endocyclic double bonds and gives the 3-cyclopentenones via the unstable epoxides.
摘要
从6-(2-羟乙基)-6-甲基富烯出发，开发了一种新的高效合成6-甲基-6-乙烯基富烯的方法。手头有了大量的目标化合物后，研究了其与单线态氧的光氧化反应。观察到环丙烷酮中间体在不饱和体系中与两个乙烯基部分发生环化反应，而饱和内过氧化物主要生成环戊烯酮衍生物。间氯过氧苯甲酸仅进攻内环双键，并通过不稳定的环氧化物生成3-环戊烯酮。
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