Generation of allenylthioketene S,S-dioxides through [3,3] sigmatropic rearrangement of alkynyl propargyl sulfones

被引：8
|
作者：
Aoyagi, Shigenobu [1 ]
Koyanagi, Makoto [1 ]
Takahashi, Megumi [1 ]
Shimada, Kazuaki [1 ]
Takikawa, Yuji [1 ]
机构：
[1] Iwate Univ, Fac Engn, Dept Chem Engn, Morioka, Iwate 0208551, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 11期
关键词：
D O I：
10.1016/j.tetlet.2007.01.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thioketene S,S-dioxides 2 were successfully generated through [3,3] sigmatropic rearrangement of alkynyl propargy] sulfones 1 and the formation of 2 was confirmed by trapping experiment using cyclohexene or allyltrimethylsilane affording a [2+2] cycloadduct 5. In situ generated thioketene S,S-dioxides 2 underwent facile conversion into allenynes 3 in moderate yields, via formation and subsequent [1,2] shift of vinylidene carbenes. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：1915 / 1918
页数：4
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