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Synthesis of Dihydrothiophenes and Thiophenes by the Strategic Use of 2‐Vinylidene‐1,3‐dithiolane as a Masked Thiolate Anion
Author(s) -
Fang Zhongxue,
Liao Peiqiu,
Yang Zonglian,
Wang Yeming,
Zhou Biying,
Yang Yang,
Bi Xihe
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301624
Subject(s) - chemistry , moiety , dithiolane , fragmentation (computing) , tandem , alkyne , sulfur , annulation , ion , combinatorial chemistry , medicinal chemistry , polymer chemistry , stereochemistry , organic chemistry , catalysis , materials science , computer science , composite material , operating system
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.