Synthesis of Dihydrothiophenes and Thiophenes by the Strategic Use of 2-Vinylidene-1,3-dithiolane as a Masked Thiolate Anion

Differently substituted 4‐(1,3‐dithiolan‐2‐ylidene)but‐1‐ynes were conveniently converted into the corresponding thiophenes and dihydrothiophenes in good to high yields under mild conditions. 1,3‐Dithiolan‐2‐ylidene acted as a masked thiolate anion and underwent tandem fragmentation and 5‐exo‐dig an...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-02, Vol.2014 (5), p.924-927
Main Authors: Fang, Zhongxue, Liao, Peiqiu, Yang, Zonglian, Wang, Yeming, Zhou, Biying, Yang, Yang, Bi, Xihe
Format: Article
Language:English
Subjects:
Annulation
Dithioacetals
Fragmentation
Ketenes
Sulfur heterocycles
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Summary:Differently substituted 4‐(1,3‐dithiolan‐2‐ylidene)but‐1‐ynes were conveniently converted into the corresponding thiophenes and dihydrothiophenes in good to high yields under mild conditions. 1,3‐Dithiolan‐2‐ylidene acted as a masked thiolate anion and underwent tandem fragmentation and 5‐exo‐dig annulation with an alkyne moiety to form the five‐membered sulfur heterocycles. An efficient and atom‐economic approach for the preparation of densely functionalized 2,3‐dihydrothiophenes and thiophenes is reported. For the first time, the strategic use of 1,3‐dithiolan‐2‐ylidene as a masked thiolate anion is used in a tandem fragmentation and 5‐exo‐dig annulation with an alkyne moiety to form five‐membered sulfur heterocycles.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301624