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

被引：17
作者：
Aoyagi, Shigenobu
Makabe, Muneyoshi
Shimada, Kazuaki
Takikawa, Yuji
Kabuto, Chizuko
机构：
[1] Iwate Univ, Fac Engn, Dept Chem Engn, Morioka, Iwate 0208551, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 26期
关键词：
D O I：
10.1016/j.tetlet.2007.04.055
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thermal reaction of alkynyl propargyl sulfoxides 1 afforded novel highly reactive (alpha-ketovinyl)thioketenes 3. Trapping experiments using a primary or secondary amine, formation of furanophane 4, through head-to-tail type dimerization, as well as direct observation using H-1 NMR elucidated the generation pathway of 3 through sequential [2,3]/[3,3] sigmatropic rearrangement. 2007 Elsevier Ltd. All rights reserved.
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页码：4639 / 4642
页数：4
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