Synthesis of (Thio)substituted-1,3-butadienes and-butenynes
Journal of the Turkish Chemical Society, Section A: Chemistry, cilt.6, sa.2, ss.201-206, 2019 (Scopus, TRDizin)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 6 Sayı: 2
- Basım Tarihi: 2019
- Doi Numarası: 10.18596/jotcsa.536853
- Dergi Adı: Journal of the Turkish Chemical Society, Section A: Chemistry
- Derginin Tarandığı İndeksler: Scopus, TR DİZİN (ULAKBİM)
- Sayfa Sayıları: ss.201-206
- Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
- İstanbul Üniversitesi-Cerrahpaşa Adresli: Hayır
Özet
© 2019, Turkish Chemical Society. All rights reserved.In this study, 2H-1,1,3,4,4-pentachloro-1,3-butadiene (1) was 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. 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 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 several methods, mass spectrometry (GC-MS(+EI)),1H-,13C-, APT-NMR, FTIR and elemental analysis.