Tez özetleri Astronomi ve Uzay Bilimleri Anabilim Dalı

The Synthesıs Of New Thıoethers From Halodıenes

Our investigations started with the synthesis of polyhalogenated butenes 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-buta-1,3-dien (6).

In the following step, reactions of thiols with the compound (6) were investigated. Therefore, 4-bromo-1-decylthio-2-nitro-1,3,4-trichloro-buta-1,3-dien (15) and 4-bromo-1-(4-bromophenylthio)-2-nitro-1,3,4-trichloro-buta-1,3-dien (17) were synthesized from the reactions of 4-bromo-2-nitro-1,1,3,4-tetrachloro-buta-1,3-dien (6) with 1-decanethiol and p-bromothiophenol, respectively.

In the last step, reactions of morpholine and derivatives of piperazine with the mono(thio)substituted nitrodien compounds were explored.

To obtain 4-bromo-1-decylthio-1-[N-(diphenylmethyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (19), 4-bromo-1-decylthio-1-[N-(2-fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (21), 4-bromo-1-decylthio-1-morpholine-2-nitro-3,4-dichloro-buta-1,3-dien (23), 4-bromo-1-decylthio-1-[N-(2-metoxyphenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (25), 4-bromo-1-decylthio-1-[N-etoxycarbonyl-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (27), 4-bromo-1-decylthio-1-[N-(4- fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (29) and 4-bromo-1-decylthio-1-(N-phenylpiperazine)-2-nitro-3,4-dichloro-buta-1,3-dien (31), the reactions of 4-bromo-1-decylthio-2-nitro-1,3,4-trichloro-buta-1,3-dien (15) with the N-(diphenylmethyl)-piperazine (18), N-(2-fluorophenyl)-piperazine (20), morpholine (22), N-(2-metoxyphenyl)-piperazine (24), N-etoxycarbonyl-piperazine (26), N-(4-fluorophenyl)-piperazine (28) ve N-phenylpiperazine (30) were performed, respectively.

Analogously, 4-bromo-1-(4-bromophenylthio)-1-[N-(diphenylmethyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (32), 4-bromo-1-(4-bromophenylthio)-1-[N-(2-fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (33), 4-bromo-1-(4-bromophenylthio)-1-morpholine-2-nitro-3,4-dichloro-buta-1,3-dien (34), 4-bromo-1-(4-bromophenylthio)-1-[N-(2-metoxyphenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (35), 4-bromo-1-(4-bromophenylthio)-1-[N-etoxycarbonyl-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (36), 4-bromo-1-(4-bromophenylthio)-1-[N-(4- fluorophenyl)-piperazine]-2-nitro-3,4-dichloro-buta-1,3-dien (37) and 4-bromo-1-(4-bromophenylthio) -1-(N-phenylpiperazine)-2-nitro-3,4-dichloro-buta-1,3-dien (38) were synthesized by the interaction of 4-bromo-1-(4-bromophenylthio)-2-nitro-1,3,4-trichloro-buta-1,3-dien (17) with the N-(diphenylmethyl)-piperazine (18), N-(2-fluorophenyl)-piperazine (20), morpholine (22), N-(2-metoxyphenyl)-piperazine (24), N-etoxycarbonyl-piperazine (26), N-(4-fluorophenyl)-piperazine (28) ve N-phenylpiperazine (30), respectively.

Synthesized two mono(thio)nitrobuta-1,3-dien compounds and their fourteen piperazine derivatives are original. The novel products were purified either crystallization or via column chromatography. Structure of these novel products were characterized by microanalysis, spectroscopic methods (IR, ¹H-NMR, ¹³C-NMR, UV and MS).


YILDIZ Mahmut,

Danışman : Prof.Dr. Cemil İBİŞ

Anabilim Dalı : Kimya

Programı (Varsa) : Organik Kimya

Mezuniyet Yılı : 2007

Tez Savunma Jürisi : Prof.Dr. Cemil İBİŞ (Danışman)

Prof.Dr. Süleyman TANYOLAÇ

Prof.Dr. F.Serpil GÖKSEL

Prof.Dr. Ahmet AKAR

Prof.Dr. Hacı ORAK