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Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu

Guoting Zhang, Hong Yi, Hong Chen, Changliang Bian, Chao Liu* and Aiwen Lei*

*College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. China, Email: chao.liuwhu.edu.cn, aiwenleiwhu.edu.cn

G. Zhang, H. Yi, H. Chen, C. Bian, C. Liu, A. Lei, Org. Lett., 2014, 16, 6156-6159.

DOI: 10.1021/ol503015b (free Supporting Information)


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Abstract

The interaction between elemental sulfur and NaOtBu enables a facile single-step protocol for the synthesis of thiophene derivatives from 1,3-diynes. A plausible mechanism based on EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process.

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Key Words

thiophenes


ID: J54-Y2014