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

Year 2019, Volume: 6 Issue: 2, 201 - 206, 15.06.2019

Aysecik Kacmaz

https://doi.org/10.18596/jotcsa.536853

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

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