Tez özetleri Astronomi ve Uzay Bilimleri Anabilim Dalı

The Synthesis of S- and N,S- Substituted Thioethers From Bromo and Chloro-2-Nitrodiene

Our investigations started with the synthesis of polyhalogenated butene which is easily obtained from the radical dimerization of trichloroethylene and its subsequent reactions leading to the compound 4-bromo-2-nitro-1,1,3,4-tetrachloro-1,3-butadiene (6).

In the following step, reactions of the compound with thiols (6) were investigated. Therefore, 4-bromo-1-cyclohexylthio-2-nitro-1,3,4-trichloro-1,3-butadiene (8) and 4-bromo-1- dodecylthio-2-nitro-1,3,4-trichloro-1,3-butadiene (10) were synthesized from the reactions of 4-bromo-2-nitro-1,1,3,4-tetrachloro-1,3-butadiene (6) with 1-cyclohexylthiol and 1-dodecanethiol respectively.

In the last step, reactions of piperazine derivatives with the mono(thio)substituted nitrodiene compounds were studied.

To obtain 4-bromo-1-cyclohexylthio-1-[N-(diphenylmethyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (12), 4-bromo-1-cyclohexylthio-1-[N-(2-fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (14), 4-bromo-1-cyclohexylthio-1-[N-(4- fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (16) and 4-bromo-1- cyclohexylthio-1-(N-phenylpiperazine)-2-nitro-3,4-dichloro-1,3-butadiene (18), the reactions of 4-bromo-1- cyclohexylthio-2-nitro-1,3,4-trichloro-1,3-butadiene (8) with the N-(diphenylmethyl)-piperazine (11), N-(2-fluorophenyl)-piperazine (13), N-(4-fluorophenyl)-piperazine (15) ve N-phenylpiperazine (17) were performed, respectively.

Analogously, 4-bromo-1-dodecylthio-1-[N-(diphenylmethyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (19), 4-bromo-1-dodecylthio-1-[N-(2-fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (20), 4-bromo-1-dodecylthio-1-[N-(4- fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (21), 4-bromo-1-dodecylthio-1-(N-phenylpiperazine)-2-nitro-3,4-dichloro-1,3-butadiene (22) 4-bromo-1-dodecylthio-1-[N-(2-metoxyphenyl)-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (24) and 4-bromo-1-dodecylthio-1-[N-etoxycarbonyl-piperazine]-2-nitro-3,4-dichloro-1,3-butadiene (26) were synthesized by the interaction of 4-bromo-1- dodecylthio-2-nitro-1,3,4-trichloro-1,3-butadiene (10) with the N-(diphenylmethyl)-piperazine (11), N-(2-fluorophenyl)-piperazine (13), N-(4-fluorophenyl)-piperazine (15) ve N-phenylpiperazine (17), N-(2-metoxyphenyl)-piperazine (23) and N-etoxycarbonyl-piperazine (25) respectively.

Synthesized one of the mono(thio)nitro-1,3-butadiene compound and ten piperazine derivatives are original. The novel products were purified either crystallization or via column chromatography. Structures of these novel products were characterized by microanalysis, spectroscopic methods (IR, 1H-NMR, 13C-NMR, UV and MS).

BİRDAL Arzu
Danışman : Doç. Dr. Cemal ÖZEROĞLU

Anabilim Dalı : Kimya

Programı : Fiziksel Kimya

Mezuniyet Yılı : 2008

Tez Savunma Jürisi : Doç. Dr. Cemal ÖZEROĞLU (Danışman)

Prof. Dr. Saadet PABUCCUOĞLU

Doç. Dr. Gülten GÜRDAĞ

Doç. Dr. Gül HİSARLI

Yrd. Doç. Dr. Gönül KEÇELİ