Novel generation of (α-ketovinyl)thioketenes as intermediates through tandem [2,3]/[3,3] sigmatropic rearrangement of alkynyl propargyl sulfoxides

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• 作者：Shigenobu Aoyagi ; Muneyoshi Makabe ; Kazuaki Shimada ; Yuji Takikawa ; Chizuko Kabuto
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：25 June 2007
• 卷：48
• 期：26
• 页码：4639-4642
• 文件大小：316 K

摘要

Thermal reaction of alkynyl propargyl sulfoxides trong>1trong> afforded novel highly reactive (α-ketovinyl)thioketenes trong>3trong>. Trapping experiments using a primary or secondary amine, formation of furanophane trong>4trong>, through head-to-tail type dimerization, as well as direct observation using ¹H NMR elucidated the generation pathway of trong>3trong> through sequential [2,3]/[3,3] sigmatropic rearrangement.