Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

Abstract

In this study, 2H-1,1,3,4,4-pentachloro-1,3-butadiene (1) reacted with different thiols (2-Methyl-2-propanethiol 2a, Benzyl mercaptan 2b, 4-tert-butylbenzenethiol 2c, 4-Nitrothiophenol 2d) in ethanol in the presence of NaOH to afford mono-thio-substituted-1,3-butadienes and mono- and tris-thio-substituted-1-buten-3-ynes. Among them, (4-tert-butylphenyl)(1,3,4,4-tetrachlorobuta-1,3-dienyl)sulfane (4c) exhibited two isomers of mono products. And, the reaction of compound (1) with 2-Hydroxythiophenol (2e) in dimethylformamide in the presence of triethylamine took place formation of OH protected butadiene structure 2-((Z)-1,3,4,4-tetrachlorobuta-1,3-dienylthio)phenol (4e) and ring-closed butadiene structure (E)-2-(2,3,3-trichloroallylidene)benzo[d][1,3]oxathiole (6), together and with two isomers of each. Their structures identified on the basis of GC-MS(+EI) analysis with different retention times (RT). Characterization of the synthesized compounds was done using different methods, mass spectrometry (GC-MS(+EI)), ¹H-, ¹³C-, APT- NMR, IR and elemental analysis.

 

Keywords

• Thioethers,1-buten-3-ynes,1,3-butadienes,GC-MS,thiols

References

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