Synthesis of α-cyano sulfone via thermal rearrangement of 1,4-disubstituted triazole mediated by carbene and radical species

A novel metal-free rearrangement of 4-substituted 1-sulfonyl-1,2,3-triazoles producing α-cyano sulfones in satisfactory yields is reported. A series of control experiments have been conducted. Carbene and radical species were proposed as the key intermediates and ketenimine was captured by an intram...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-02, Vol.7 (3), p.596-601
Main Authors: Cen, Mengjie, Xiang, Qiaoyi, Xu, Yiwen, Duan, Shengguo, Lv, Yaohong, Ze-Feng Xu, Chuan-Ying, Li
Format: Article
Language:English
Subjects:
Crystallography
Intermediates
Organic chemistry
Sulfones
Triazoles
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Summary:A novel metal-free rearrangement of 4-substituted 1-sulfonyl-1,2,3-triazoles producing α-cyano sulfones in satisfactory yields is reported. A series of control experiments have been conducted. Carbene and radical species were proposed as the key intermediates and ketenimine was captured by an intramolecular reaction. This process is fundamentally different from that reported in the literature which produces the same product. Several fused multi-cycle compounds could be constructed efficiently.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01340g