Stepwise Cycloadditions of Mesoionic Systems: Thionation of Thioisomünchnones by Isothiocyanates

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• 作者：David Cantillo ; Mart&iacute ; n Á ; valos ; Reyes Babiano ; Pedro Cintas ; José ; L. Jimé ; nez ; Mark E. Light ; Juan C. Palacios
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：March 20, 2008
• 年：2008
• 卷：10
• 期：6
• 页码：1079 - 1082
• 全文大小：132K
• 年卷期：v.10,no.6(March 20, 2008)
• ISSN：1523-7052

文摘

LE>l702929kn00001>ls/orlef7/10/i06/figures/ol702929kn00001.gif" ALIGN="left" HSPACE=5>An unusual thionation strategy of mesoionic compounds with aryl isothiocyanates enables a facile synthesis of 1,3-thiazolium-4-thiolate systems.The mechanistic pathway of such a transformation most likely involves a stepwise 1,3-dipolar cycloaddition, which is supported by theoreticalcalculations performed with a two-layer hybrid method (B3LYP/6-31G(d):PM3).