Bazı poli(organilthio)-1-3-butadien bileşiklerinin sentezi

Abstract

V. ÖZET Bası PoIi(orgsmitiiio)-l/3-butadiea Bileşiklerisin Seatezi 3,3-Dikloıakrolein'in trMonnetiîlityurn il© reaksiyonundan 2,3-Di-H- heksaklorbuten-1 kazanıldı. Daha sonra bu bileşiğin DMF'te trietilamin varlığında ve DMF'te NaOH varlığında tiyollerle (tiyofenol, p-klortiyofenol, 2,6-diklortiyofenol, p- metiltiyofenol) reaksiyonundan baa poli(organiltiyo>l,3-butadien bileşikieri elde edildi. 2,3-Di-H-h.eksaklorbuten-l ile îiyofenolûn DMF'te trietilamin varlığındaki reaksiyonundan; l,4-dMor-l,44)is(fenütiyo)-l,3-buiadien (1), l,î,4,4-tetrakis(fe- niltiyo)-l,3-butadien (2) bileşikleri; DMF'te NaOH varlığındaki reaksiyonundan da l,4-diklor-l,4-bis(feniltiyo)-l,3-butadien (1), 14,4,44etrakis(feniltiyo>l,3-butadien (2), bis(fenil)-disulfîd (3) bileşikleri elde edildi. 2,3-Di-H-heksaklorbuten-l ile p-klortiyofenolün DMF'te trietilamin varlığındaki reaksiyonundan; lj,4,4-tetrakk(4-klorferültiyo)-l,3-butadien (S), 1-klor- l,4J4-tris(4-klorfeniltryo)-l,3-butadien (7) bileşikleri; DMF'te NaOH varlığındaki reaksiyonundan da 14,4,4-tetrakk(4-Moıfeniltiyo)-l,3-butadien (S), bis(4-klorfenil)- disülfid (9) bileşikleri kazanıldı. 2,3-Di-H-heksaklorbuten-l ile 2,6-dMortryofenolün DMF'te trietilamin varlığındaki reaksiyonundan l,4niiMor-î,4-bİ8(2,6KİiMorfeniltryo)-l,3-butadien {Iff) elde edildi. 2,3-Di-H-hek3aklorbuten-l ile p-meültiyofenolün DMF'te trietilamin varlığındaki reaksiyonundan; l,4-ciMOT-l,4-big^metilfeniltiyo)-l,3-butadien (II) ve 14,4,4-tetrakis(p-metiîferaltiyo>l,3-butadien (12) bileşikleri; DMF'te NaOH varlığındaki reaksiyonundan da l,4-diMor-l,4-bis(r>metiîtenütryo)-l,3-buîadien (II), bis(p-metilfenil)-disülfid (İS) bileşikleri kazanıldı. Elde edilen bileşiklerin yapılan mikroaraîiz ve spektroskopik yöntemlerle ('H-NMR, İR spektroskopisi) aydınlatıldı. 61

V. SUMMARY The Synthesis of Some PolyCorgaaykhioJ-l^S-biitadieae Compounds 2,3-Di-H-hexachlorbutene-l was prepared from reaction of 3,3-dichloracrolein with trichlocmethyllithium. Then, some poly(organylthio)-l,3-butadien.e compounds were obtained from reaction with thiols (thiophenol, p-chlorthiophenol, 2,6-dichlor- thiophenol, p-methylthiophenoi) of this compound in the presence of triethylamine and ofNaOHinDMF. l,4-Dichior-l,4-bis(phenylthio)-l,3-butadiene (1), l,l,4,4-tettafcis(phenyithio)- 1,3-butadiene (2) compounds were obtained from reaction of thiophenol with 2,3-Di- H-hexachlorbutene-l in the presence of triethylamine in DMF; l,4-dichlor-l34- bis(phenylthio)-l,3-butadiene (1), l,l,4,4-tetrakis(phenylthiQ)-l,3-butadiene (2), bis(phenyl)-disulfide (3) compounds were obtained, when the same reaction was applied in the presence of NaOH in DMF, as well. lJ,4,4-Tetokk(4-cHoiphenylthio)-l,3-butadiene (5), l-chİQr-l.,4,4-tris(4- chloTphenylthio)-l,3-butadiene (7) compounds were prepared from reaction of p- chlorthiophenol with 2,3-Di-H-hexachlorbutene-l in the presence of triethylamine in DMF; l,l,4,4-tetrakis(4-chlorphenylthio)-l,3-butadiene (-5), bis(4-chloiphenyl)- disulfide (9) compounds were obtained, when the same reaction was applied in the presence of NaOH in DMF, too. l,4-DicMor-l,4-bis(2,6-dicHorphenylthio)-l,3-butadiene (10) was obtained from reaction 2,6-dichlorthiophenol with 2,3-Di-H-hexachlorbutene-l in the presence of triethylamine in DMF. l,4-Dichlor-l,4-bis(p-methylphenylthio)-l,3-butadiene (11) and 1,1,4,4- îetrakkip-methyiphenyîthio)- 1,3 -butadiene (12) compounds were prepared from reaction of p-methylthiophenol with 2,3-Di-H-hexachlorbutene-l in the presence of triethylamine in DMF. When the same reaction was applied in the presence of NaOH in DMF, l^-dicWor-l^bisCp-methylphenylthio^Vl^-butadiene (11), bis(p-methyl- phenyl)-disrulfide (IS) compounds were prepared, as well.The structure of the obtained compounds were determined by microanalysis and spectroscopic methods (TH-NMR, IR spectroscopy). 63