Synthesis of bicyclo[3.2.1]octanones via ketyl radical promoted rearrangements under reductive PET conditions

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• 作者：Somnath Yadav ; Srirupa Banerjee ; Dwijendralal Maji ; Saswati Lahiri
• 关键词：Bicyclo[3.2.1]octanones ; Cyclopropyl ring cleavage ; Photoinduced electron transfer (PET)
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：5 November 2007
• 卷：63
• 期：45
• 页码：10979-10990
• 文件大小：473 K

摘要

Photoinduced electron transfer (PET) reactions from triethylamine (TEA) to ketones have been utilized for a clean and efficient route to bicyclo[3.2.1]octanones. A one-pot conversion of bicyclo[2.2.2]octenones to such molecules has been described. MeOH as well as acetonitrile/LiClO₄ combinations have been found to be the most effective solvents for these reactions.