Room-Temperature and Metal-Free
Synthesis of 1,1-Dithio-1-alkenes from 1,1-Dibromo-1-alkenes and
Thiols

Hui Jin; Yiwen Yang; Chunxiang Kuang; Qing Yang

doi:10.1055/s-0031-1289872

LETTER

Room-Temperature and Metal-Free Synthesis of 1,1-Dithio-1-alkenes from 1,1-Dibromo-1-alkenes and Thiols

Hui Jin^a, Yiwen Yang^a,b, Chunxiang Kuang*^a, Qing Yang*^c
^a Department of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China
Fax: +86(21)65983191; e-Mail: kuangcx@tongji.edu.cn;
^b School of Biology and Chemical Engineering, Jiaxing University, Jiaxing 314001, P. R. of China
^c Department of Biochemistry, School of Life Sciences, Fudan University, Handan Road 220, Shanghai 200433, P. R. of China
Fax: +86(21)65643446; e-Mail: yangqing68@fudan.edu.cn;

Abstract

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Abstract

An efficient metal-free synthesis of 1,1-dithio-1-alkenes from 1,1-dibromo-1-alkenes and thiols using a diazabicycloundecene/dimethyl sulfoxide system was developed. The method was found suitable for various 1,1-dibromo-1-alkenes. The synthesis was completed within 5-15 minutes at room temperature with moderate to excellent yields.

Key words

room temperature - metal-free - 1,1-dithio-1-alkenes - 1,1-dibromo-1-alkenes - thiols

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References

References and Notes

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General Procedure for the Synthesis of 3 DMSO (3 mL), 1,1-dibromo-1-alkenes 1 (0.3 mmol), DBU (1.05 mmol), and thiols 2 (0.66 mmol) were placed in a sealed tube. The mixture was stirred at r.t., and the reaction was monitored by TLC. After the reaction was completed, the system was extracted with Et₂O (3 × 25 mL). The combined organic layer was washed with H₂O and was dried over MgSO₄. The solvent was evaporated, and the crude product was purified by silica gel column chromatography to yield 1,1-dithio-1-alkenes 3.
Selected Data[2-(4-Isopropylphenyl)ethene-1,1-diyl]bis( p -tolyl-sulfane) (3a)
Light yellow solid. ^¹H NMR (400 MHz, CDCl₃): δ = 7.53 (d, J = 7.5 Hz, 2 H), 7.39 (d, J = 8.0 Hz, 2 H), 7.23-7.14 (m, 8 H), 6.98 (d, J = 8.0 Hz, 2 H), 2.34 (s, 3 H), 2.22 (s, 3 H).

Supplementary Material

Supporting Information (PDF)