Synthesis 2016; 48(18): 3107-3119
DOI: 10.1055/s-0035-1561452
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Symmetrical and Unsymmetrical 1,4-Dithiins by Rhodium-Catalyzed Sulfur Addition Reaction to Alkynes

Mieko Arisawa*
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Sendai, 980-8578, Japan   eMail: yama@m.tohoku.ac.jp   eMail: arisawa@m.tohoku.ac.jp
,
Takuya Ichikawa
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Sendai, 980-8578, Japan   eMail: yama@m.tohoku.ac.jp   eMail: arisawa@m.tohoku.ac.jp
,
Saori Tanii
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Sendai, 980-8578, Japan   eMail: yama@m.tohoku.ac.jp   eMail: arisawa@m.tohoku.ac.jp
,
Masahiko Yamaguchi*
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Sendai, 980-8578, Japan   eMail: yama@m.tohoku.ac.jp   eMail: arisawa@m.tohoku.ac.jp
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Publikationsverlauf

Received: 15. März 2016

Accepted after revision: 10. April 2016

Publikationsdatum:
19. Mai 2016 (online)


Abstract

A convenient synthetic method for 1,4-dithiins was developed using sulfur and alkynes. A rhodium complex catalyzes the addition reaction of sulfur with cyclic alkynes giving the corresponding symmetrical 1,4-dithiines under reflux conditions in 2-butanone. Unsymmetrical 1,4-dithiins are synthesized by the reaction of sulfur with dialkyl acetylenedicarboxylates in the presence of cyclic alkynes or vinyl ethers.

Supporting Information

 
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