Bis fenol tiyofenlerin Stille Coupling reaksiyonu ile sentezlenmesi
Synthesis of bis phenol tiophen with Stille Coupling reaction
- Tez No: 142677
- Danışmanlar: DOÇ. DR. OKAN SİRKECİOĞLU
- Tez Türü: Yüksek Lisans
- Konular: Kimya, Chemistry
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 2003
- Dil: Türkçe
- Üniversite: İstanbul Teknik Üniversitesi
- Enstitü: Fen Bilimleri Enstitüsü
- Ana Bilim Dalı: Kimyagerlik Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 82
Özet
Bu çalışmada mono ve di bisfenol tiyofenlerin sentezi palladyum(0) katalizatörlüğünde Stille Coupling reaksiyonu ile gerçekleştirildi. Stille reaksiyonunun gerçekleştirilebilmesi için reaktanlardan bir tanesi kalay türevine dönüştürülürken diğer reaktant ise halojenür yada kolay ayrılan gruplardan bir tanesini bağlanmanın gerçekleştirileceği konumda içermelidir. \"/ SnBu3 ~\J ')OCH3 n Pd
Özet (Çeviri)
In this study mono and di bisphenol thiophen compounds were synthesized by Stille Coupling reaction with palladium(0) catalyst. In stille reactions one of the reactant must be converted to its tin derivative while other reactant include halogen or other easy leaving group that copling occurs. 2 - h,co In our study we use first metot because of, having p-bromoanisole in our laboratory and it is easier to convert thiophen to its tin derivative than that of the benzene. To synthesize mono bisphenol thiophen, thiophen converted its tin derivative at C(2) position treated with tributiltin chloride.SnBu3 Pd ( O ), tolüen reflux, 12 hours OCH, OCH-, In the result of this stille reaction 2 - (4 - methoxyphenyl) thiophen was obtained. This compound is very important for synthesize of both mono and di bisphenol thiophen. Second step of synthesizing of mono bisphenol thiophen is converting 2 - (4 - methoxyphenil) thiophen to its tin derivative at C(5) position treated by with tributiltinchoride to obtain 2 - (4 - methoxyphenyl) 5- tributyltin thiophen. In- BuLi 2(Bu)^SnCl OCH3 o C, 2 hour BugSn OCH, After this reaction 2 - (4 - methoxyphenil) 5- tributiltin thiophen treated stille- coupling reaction with p - bromo anisole under catalyst of tetrakistriphenilphosphine palladium(O). In the result of this reaction we obtained methoxy derivative of mono bisphenol thiophen which is called 2,5 bis(4-methoxyphenil) thiophen. Bi%Sn OCH, Pd(0) tolüen reflux 16 hours Br/ Yoch, OCtJ For synthesize of bisphenol dithiophen, 2 - (4 - methoxyphenil) thiophen that is synthesize before, treated with NBS to bromined C(5) position of thiophen. After converting 2 - (4 - methoxyphenil) thiophen to its halogen derivative its treated with 2 - (4 - methoxyphenil) 5 - tributiltin thiophen which is synthesized in synthesis of mono bisphenol thiophen, under catalyst of tetrakistriphenilphosphine palladium(O) for stille coupling reaction. After purification methoxy derivative of bisphenol dithiophen were obtained. xiNBS, DMF OCH3 20 C, 4 hours OCH, Bu3Sn OCH3 Pd ( 0 ) toiüen reflux, 20 hours %40 OCH., This study was concluded with, converting existing methoxy derivatives to bis phenol form by treated with pyridine hydrochloride. piridin hidroklorür
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