Mono-, bis-, tris-, and tetrakis(thio)substituted butenynes from halogenated butenes and butadienes

Ibis, Cemil; Ayla, Sibel Sahınler

doi:10.1080/10426507.2017.1308935

Cited by 1 publication

(2 citation statements)

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“…Reactions of polyhalo-dienes and -butenes with thiols or amines have been previously reported by Ibis and co-workers and Roedig and coworkers (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). Yoshimatsu et al reported the preparation of 2-sulfonyl-1-buten-3-ynes and their reactions with nucleophiles (9).…”

Section: Introductionmentioning

confidence: 84%

“…It is reported by our laboratory, that the reaction between 1 and different thiols under mild conditions results the formation of thiosubstituted 1,3-butadienes/butenynes (12)(13)(14). Among them, in 2010 (19) and 2016 (20), we reported that some mono-, bis-, tris-and tetrakis-substituted butenynes, butadienes or buta-1,2,3-trienes and their halogenation (iodination/bromination) and oxidation of some butadienes to their corresponding sulfoxides or sulfones.…”

Section: Introductionmentioning

confidence: 91%

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

Kaçmaz

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, 2H-1,1,3,4,4-pentachloro-1,3-butadiene (1) was reacted with different thiols (2methyl-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-thiosubstituted-1-buten-3-ynes. Among them, (4-tert-butylphenyl)(1,3,4,4-tetrachlorobuta-1,3dienyl)sulfane (4c) exhibited two isomers of mono products. Moreover, the reaction of compound (1) with 2-hydroxythiophenol (2e) in dimethylformamide in the presence of triethylamine took place the formation of OH-protected butadiene structure 2-((Z)-1,3,4,4-tetrachlorobuta-1,3-dienylthio)phenol (4e) and ringclosed 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 several methods, mass spectrometry (GC-MS(+EI)), 1 H-, 13 C-, APT-NMR, FTIR and elemental analysis.

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