Doymamış gruplu bazı yeni tiyoeterlerin sentezi
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Abstract
DOYMAMIŞ GRUPLU BAZI YENİ TIYOETERLERİN SENTEZİ ÖZET Bu çalışmada ilk aşama olarak trikloretilenin dimerleşmesi ile hazırlanan 2-Nitro- pentaklor-l,3-butadien (1) bileşiği elde edildi. Çalışmanın İkinci aşamasında 2-Nitro-pentaklor-l,3-butadien (1) bileşiği başlangıç maddesi olarak kullanıldı ve 4-fluorotiyofenol ile reaksiyona sokuldu. Bu reaksiyon sonucunda l,3,4,4-tetraWor-l-(fluorofeniltiyo)-2-nitro-l,3-butadien (2) bileşiği elde edildi. Üçüncü aşamada elde edilen l,3,4,4-tetraklor-l-(fluorofeniltiyo)-2-nitro-l,3- butadien (2) bileşiği bazı N-nükleofillerle reaksiyona sokuldu. 1,3,4,4-tetraklor-l- (ıluorofeniltiyo)-2-nitro-l,3-butadien (2) bileşiği sırasıyla N-fenilpiperazin, l-(4- fluorfenil)-piperazin, 1-metilpiperazin, morfolin, p-aminobenzotrilluorür, p-fluoranilin, piperidin, 4-metilpiperdin, 1 -etoksikarbonilpiperazin, l-(2-hidroksietil)-piperazin, 4- benzüpiperidin, piperidinol, 2,5-dimetilpiperazin, piperazin ile reaksiyona sokuldu. Reaksiyon sonucunda sırasıyla l-(3,4,4,-trMor-l-(4-fluorofeniltiyo)-2-nitro-l,3- butadienil)-4-fenilpiperazin (3), l-(3,4,4-triklor-l-(4-fluoro- feniltiyo)-2-nitro-l,3-buta- dienill)-4-(4-fluorofenil)-piperazin (4), 1 -(3,4,4-triklor- 1 -(4-fluorofeniltiyo)-2-nitro- 1,3 - butadienil)-4-metilpiperazin(5), 3,4,4-triklor-l-(morfolino)-l-(4-fluoro±eniltiyo)-2-nitro - 1,3-butadien (6), 3,4,4-triklor- 1 -(p-fluorofeniltiyo)- 1 -(4-aminobenzotrifluoro)-2-nitro- 1,3-butadien (7), 3,4,4-triklor-l-(p-fluoroteniltiyo)-l-(4-fluorotenilamino)-2-nitro-l,3- butadien (8), 3,4,4-triklor- 1 -(p-fluorofeniltiyo)- l-(piperidino)-2-nitro-l,3-butadien (9),3,4,4-triklor- 1 -(p-fluorofeniltiyo)-l -(4-metilpiperidino)-2-nitro- 1,3-butadien (10), l-(2- nitro-3,4,4-triklor- 1 -(4-fluorofeniltiyo)- 1,3-butadienil)-4-(etoksikarbonil)-piperazin( 1 1), l-(2-nitro-3,4,4-triklor-l-(4-fluorofeniltiyo)-l,3-butadienil)-4-(2-hidroksietil)-piperazin (12), 3,4,4-triklor- 1 -(4-tluorofeniltiyo)- 1 -(4-benzilpiperidino)-2-nitro- 1,3-butadien (13), 1 -(4-fluoroleniltiyo)- 1 -(4-hiroksipiperidino)-2-nitro-3,4,4-trikloro- 1,3-butadien (14), N- [l-(4-fluorofeniltiyo)-2-nitro-3,4,4-trMoro-l,3-butedienil)]-2,5-dimetilpiperazin (15), N-[ 1 -(4-fluorofeniltiyo)-2-nitro-3,4,4-trikloro-l,3-butediefıil)]-piperazin (16), N,Nl-Bis -[3,4,4-triklor- 1 -(4-fîuorofeniltiyo)-2-nitro- 1,3-butadienil]-piperazin (17), N,N! -Bis-[3,4,4-triklor-l-(4-fluorofeniltiyo)-2-nitro-l,3-butadienilJ-2,5-dimetilpiperazin (18) bileşik leri sentezlendi. Elde edilen bu yeni bileşikler kristalizasyon ve kromatografık yöntemlerle saflaştırılmıştır. Yapıları spektroskopik yöntemlerle (İR, 'H-NMR, MS) aydınlatılmıştır. IX ` THE SYNTHESIS OF SOME NEW THIOETHERS HAVING UNSATURATED GROUPS ` SUMMARY In this work, firstly 2-Nitro-pentachloro- 1,3 -butadiene (1) organic compound was synthesized by dimerization of trichloroethylene. In the second step of this work, 2-Nitro-pentachlor- 1,3 -butadiene (1) was used as starting compound. In this step, S-substituted nitrodiene compound was obtained. Therefore l,3,4,4-tetrachlor-l-(fluorophenylthio)-2-nitro-l,3-butadiene (2) was obtained from the reactions of 2-Nitro-pentachlor- 1,3-butadiene (1) with 4-fluorothiophenol. In the third step, the reactions of some N-nucleophiles with 1,3,4,4-tetrachlor-l- (fluorophenylthio)-2-nitro-l,3-butadiene (2) were done. 1 -(3,4,4,-trichlor- 1 -(4-fluorophenylthio)-2-nitro- 1,3-butadienyl)-4-phenylpipera- zin (3), 1 -(3,4,4-trichlor- 1 -(4-lluoro-phenylthio)-2-nitro- 1,3-butadienyl)-4-(4-fluorophe- yl)-piperazin (4), 1 -(3,4,4-trichlor- 1 -(4-fluorophenylthio)-2-nitro- l,3-butadienyl)-4-me- thylpiperazin (5), 3,4,4-trichlor-l -(morpholino)-l -(4-fluorophenylthio)-2-nitro- 1,3-buta- dien (6), 3,4,4-trichlor- 1 -(p-fluorophenylthio)- 1 -(4-aminobenzotrifluoro)-2-nitro- 1,3- butadien (7), 3,4,4-trichlor- 1 -(p-fluorophenylthio)- 1 -(4-fluorophenylamino)-2-nitro- 1,3- butadien (8), 3,4,4-trichlor- 1 -(p-fluorophenylthio)- 1 -(piperidino)-2-nitro- 1,3-butadien (9), 3,4,4-trichlor- 1 -(p-fluorophenylthio)- 1 -(4-methylpiperidino)-2-nitro- 1,3-butadien (10), 1 -(2-nitro-3,4,4-trichlor- 1 -(4-fluorophenylthio)- 1,3-butadienyl)-4-(ethoxycarbonil) -piperazin (11), 1 -(2-nitro-3,4,4-trichlor- 1 -(4-fluorophenylthio)- 1,3-butadienyl)-4-(2- (hydroxyethyl)-piperazin (12), 3,4,4-trichlor- 1 -(4-fluorophenylthio)- 1 -(4-benzylpiperi- dino)-2-nitro- 1,3-butadien (13), 1 -(4-fluorophenylthio)- 1 -(4-hydroxypiperidino)-2-nitro -3,4,4-trichloro-l,3-butadien(14), N-[l-(4-fluorophenylthio)-2-nitro-3,4,4-trichloro-l,3- butadienyl)]-2,5-dimethylpiperazin (15), N-[ 1 -(4-fluorophenylthio)-2-nitro-3,4,4-tri- chloro-1,3-butadienyl)]-piperazin (16), N,Nl-Bis-[3,4,4-trichlor-l-(4-fluorophenylthio)- 2-nitro-L3-butadienyl]-piperazin (17), N,N'-Bis-[3,4,4-trichlor-l-(4-fluorophenylthio)- 2-nitro-l,3-butadienyl]-2,5-dimethylpiperazin (18) were synthesized from the reactions of 1, 3, 4,4-tetrachlor-l-(fluorophenylthio)-2-nitro- 1,3 -butadiene (2) with N-phenyl- piperazin, l-(4-fluorfenil)-piperazin, 1-methylpiperazin, morpholin, p-aminobenzo- trifluoride, p-fluoranilin, piperidin, 4-methylpiperdin, 1 -ethoxycarbonil-piperazin, l-(2- hydroxyethyl)-piperazin, 4-benzylpiperidin, piperidinol, 2,5-dimethyl-piperazin, pipe razin, respectively. These novel compounds were obtained that either characterized by spectroscopic methods ('H-NMR, IR, MS ). X
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