Mechanism and Regioselectivity of the Cycloaddition of Thiones Derived from Meldrum’s Acid, Malonates, or Other Dicarbonyls

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• 作者：Sté ; phane Perreault ; Maude Poirier ; Pascal Lé ; veillé ; Olivier René ; Pascal Joly ; Yves Dory ; Claude Spino
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：October 3, 2008
• 年：2008
• 卷：73
• 期：19
• 页码：7457-7466
• 全文大小：568K
• 年卷期：v.73,no.19(October 3, 2008)
• ISSN：1520-6904

文摘

Several α,α-dioxothiones were generated in situ and reacted with 1,3-dienes of varying electronic and steric properties. It was found that thiones 10a and 11a reacted well with electron-rich or electron-poor dienes and are complementary in their regioselectivities when steric effects are at play. The calculated preferred mechanistic pathway implies a thiiranium zwitterion intermediate.