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İstanbul Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Anabilim Dalı / Organik Kimya Bilim Dalı

Bazı heterosiklik gruplu tiyollerin polihalodienlerle reaksiyonları

The reactions of some thiols containing heterocyclic groups with polihalodienes

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Özet:

Bu çalışmanın ilk aşamasında 2-Nitropentaklor-1,3-butadien (1) bileşiği başlangıçmaddesi olarak elde edildi.Çalışmanın ikinci aşamasında 2-Nitropentaklor-1,3-butadien (1) bileşiği ile p-flortiyofenol, p-bromtiyofenol, p-klortiyofenol, p-metiltiyofenol, 2-naftiltiyol,sikloheksan tiyol ve benzil tiyol bileşikleriyle reaksiyona sokulmuş ve neticede bilinen1,3,4,4-Tetraklor-1-(4-florofeniltiyo)-2-nitro-1,3-butadien (2), 1,3,4,4-tetraklor-1-(4-klorofeniltiyo)-2-nitro-1,3-butadien (5), 1,3,4,4-tetraklor-1-(4-bromofeniltiyo)-2-nitro-1,3-butadien (8), 1,3,4,4-tetraklor-1-(4-metilfeniltiyo)-2-nitro-1,3-butadien (11),1,3,4,4-tetraklor-1-(2-naftiltiyo)-2-nitro-1,3-butadien (14), 1,3,4,4-tetraklor-1-sikloheksiltiyo-1,3-butadien (16) ve 1,3,4,4-tetraklor-1-benziltiyo-2-nitro-1,3-butadien(19) bileşikleri elde edildi.Çalışmanın üçüncü aşamasında ise elde edilen 1,3,4,4-tetraklor-1-(4-florofeniltiyo)-2-nitro-1,3-butadien (2), 1,3,4,4-tetraklor-1-(4-klorofeniltiyo)-2-nitro-1,3-butadien (5),1,3,4,4-tetraklor-1-(4-bromofeniltiyo)-2-nitro-1,3-butadien (8), 1,3,4,4-tetraklor-1-(4-metilfeniltiyo)-2-nitro-1,3-butadien (11), 1,3,4,4-tetraklor-1-(2-naftiltiyo)-2-nitro-1,3-butadien (14), 1,3,4,4-tetraklor-1-sikloheksiltiyo-1,3-butadien (16) ve 1,3,4,4-tetraklor-1-benziltiyo-2-nitro-1,3-butadien (19) bileşikleri tiyomorfolin ve N-difenilmetilpiperazin bileşikleri ile reaksiyona sokuldu. Reaksiyon sonucunda sırasıyla 3,4,4-trikloro-1-(4-florofeniltiyo)-1-tiyomorfolino-2-nitro-1,3-butadien (3), 1-[3,4,4-trikloro-1-(4-florofeniltiyo)-2-nitro-1,3,-butadienil]-4-difenilmetil piperazin (4), 3,4,4-triklor-1-(4-klorofeniltiyo)-1-tiyomorfolino-2-nitro-1,3-butadien (6), 1-[3,4,4-triklor-1-(4-klorofeniltiyo)-2-nitro-1,3-butadienil]-4-difenilmetil piperazin (7), 3,4,4-triklor-1-(4-bromofeniltiyo)-1-tiyomorfolino-2-nitro-1,3-butadien (9), 1-[3,4,4-triklor-1-(4-bromofeniltiyo)-2-nitro-1,3-butadienil]-4-difenilmetil piperazin (10), 3,4,4-triklor-1-(4-metilfeniltiyo)-1-tiyomorfolino-2-nitro-1,3-butadien (12), 1-[3,4,4-triklor-1-(4-metilfeniltiyo)-2-nitro-1,3-butadienil]-4-difenilmetil piperazin (13), 3,4,4-triklor-1-(2-naftiltiyo)-1-tiyomorfolino-2-nitro-1,3-butadien (15), 3,4,4-triklor-1-sikloheksiltiyo-1-tiyomorfolino-2-nitro-1,3-butadien (17), 1-[3,4,4-triklor-1-sikloheksiltiyo-2-nitro-1,3-butadienil]-4-difenilmetil piperazin (18), 3,4,4-triklor-1-benziltiyo-1-tiyomorfolino-2-nitro-1,3-butadien (20) ve 1-[3,4,4-triklor-1-benziltiyo-2-nitro-1,3-butadienil]-4-difenilmetil piperazin (21) bileşikleri sentezlendi.Elde edilen bu yeni bileşikler kromatografik yöntemlerle saflaştırılmıştır.YapılarıElemental Analiz ve spektroskopik yöntemlerle (IR, 1H-NMR) aydınlatılmıştır.

Summary:

In the first step of this study, 2-Nitropentachloro-1,3-butadiene (1) was synthesized as astarting compoundIn the second step of the study, 2-Nitropentachloro-1,3-butadiene (1) compound reactedwith p-fluorothiophenol, p-cholorothiophenol, p-bromothiophenol, p-methylthiophenol,2-naphthylthiol, cyclohexanthiol and benzylthiol and also known compounds, 1,3,4,4-tetrachloro-1-(4-fluorophenylthio)-2-nitro-1,3-butadiene (2), 1,3,4,4-tetrachloro-1-(4-chlorophenylthio)-2-nitro-1,3-butadiene (5), 1,3,4,4-tetrachloro-1-(4-bromophenylthio)-2-nitro-1,3-butadiene (8), 1,3,4,4-tetrachloro-1-(4-methylphenylthio)-2-nitro-1,3-butadiene (11), 1,3,4,4-tetrachloro-1-(2-naphthylthio)-2-nitro-1,3-butadiene (14),1,3,4,4-tetrachloro-1-cyclohexylthio-1,3-butadiene (16) and 1,3,4,4-tetrachloro-1-benzylthio-2-nitro-1,3-butadiene (19), were obtained.In the third and last step of the study, 1,3,4,4-Tetrachloro-1-(4-fluorophenylthio)-2-nitro-1,3-butadiene (2), 1,3,4,4-tetrachloro-1-(4-chlorophenylthio)-2-nitro-1,3-butadiene(5), 1,3,4,4-tetrachloro-1-(4-bromophenylthio)-2-nitro-1,3-butadiene (8), 1,3,4,4-tetrachloro-1-(4-methylphenylthio)-2-nitro-1,3-butadiene (11), 1,3,4,4-tetrachloro-1-(2-naphthylthio)-2-nitro-1,3-butadiene (14), 1,3,4,4-tetrachloro-1-cyclohexylthio-1,3-butadiene (16) and 1,3,4,4-tetrachloro-1-benzylthio-2-nitro-1,3-butadiene (19)compounds were reacted with thiamorpholine and N-diphenylmethyl piperazine Theresult of reactions respectively, 3,4,4-trichloro-1-(4-fluorophenylthio)-1-thiamorpholino-2-nitro-1,3-butadiene (3), 1-[3,4,4-trichloro-1-(4-fluorophenylthio)-2-nitro-1,3,-butadienyl]-4-diphenylmethyl piperazine (4), 3,4,4-trichloro-1-(4-chlorophenylthio)-1-thiamorpholino-2-nitro-1,3-butadiene (6), 1-[3,4,4-trichloro-1-(4-chlorophenylthio)-2-nitro-1,3-butadienyl]-4-diphenylmethyl piperazine (7), 3,4,4-trichloro-1-(4-bromophenylthio)-1-thiamorpholino-2-nitro-1,3-butadiene (9), 1-[3,4,4-trichloro-1-(4-bromophenylthio)-2-nitro-1,3-butadienyl]-4-diphenylmethyl piperazine(10), 3,4,4-trichloro-1-(4-methylphenylthio)-1-thiamorpholino-2-nitro-1,3-butadiene(12), 1-[3,4,4-trichloro-1-(4-methylphenylthio)-2-nitro-1,3-butadienyl]-4-diphenylmethyl piperazine (13), 3,4,4-trichloro-1-(2-naphtylthio)-1-thiamorpholino-2-nitro-1,3-butadiene (15), 3,4,4-trichloro-1-cyclohexylthio-1-thiamorpholino-2-nitro-1,3-butadiene (17), 1-[3,4,4-trichloro-1-cyclohexylthio-2-nitro-1,3-butadienyl]-4-diphenylmethyl piperazine (18), 3,4,4-trichloro-1-benzylthio-1-thiamorpholino-2-nitro-1,3-butadiene (20) and 1-[3,4,4-trichloro-1-benzylthio-2-nitro-1,3-butadienyl]-4-diphenylmethyl piperazine (21) compounds were synthezed.These synthezed new compounds were purified by chromatograpic methods. Thestructures of compounds were determined by micro analysis and spectroscopic methods(IR, 1H-NMR).