Hedefli Konjuge Karbonil Bileşiklerinin Sentezi Ve Reaksiyonları
Hedefli Konjuge Karbonil Bileşiklerinin Sentezi Ve Reaksiyonları
Dosyalar
Tarih
2010-07-07
Yazarlar
Akkaş, Tuğçe
Süreli Yayın başlığı
Süreli Yayın ISSN
Cilt Başlığı
Yayınevi
Fen Bilimleri Enstitüsü
Institute of Science and Technology
Institute of Science and Technology
Özet
Olcay Anaç ve ekibinin yakın çalışmalarında, hedefli seçilmiş α, β-doymamış karbonil bileşiklerinden ve metallo karbenoidlerden türetilmiş karbonil ilidlerin elektrosiklik halka kapanması reaksiyonları irdelenmektedir. Bu çalışmalarda α, β-doymamış mono/bis ketonların ve α, β-doymamış mono/bis esterlerin, Cu(acac)2 katalizörü varlığında, diazo karbonil bileşikleri ile [1,5]-elektrosiklik halka kapanması reaksiyonu üzerinden dihidrofuran türevleri ve [1,7]-elektrosiklik halka kapanması reaksiyonu üzerinden dihidrobenzoksepin türevlerinin oluşturduğu gözlenmiştir. Bu tezde öncelikle, seçilmiş m-nitro benziliden etilasetoasetat, p-nitro benziliden asetilaseton, furiliden asetilaseton, furiliden etilasetoasetat ve furiliden metilasetoasetat α, β-doymamış bis-karbonil bileşiklerinin sentezi amaçlanmıştır. Sentezi hedeflenen bis-karbonil içeren bu bileşiklerde, bis-metil keton, bis-metil keton/etil ester, bis-metil keton/metil ester fonksiyonları bulunmaktadır. Ayrıca, polimerizasyona gidemeyen α, β-doymamış monokarbonil bileşiklerin en küçük modeli olması amacıyla, etil krotonat sentezi de planlanmıştır. α, β-doymamış bis-karbonil bileşikleri ve mono-karbonil bileşiğinin yapıları, 1H NMR spektrumları ve GC-MS analizleri ile tam olarak aydınlatılmıştır. Daha sonra, sentezi başarılı olan α, β-doymamış mono/bis-karbonil bileşiklerini kullanarak Cu(acac)2 katalizörlüğündeki etil asetodiazoasetat (eada) dekompozisyon reaksiyonlarının irdelenmesi hedeflenmiştir.
In the research conducted by Olcay Anaç and her group, formal electrocyclization reactions of ylides derived from αβ-unsaturated carbonyl compounds and metallo carbenoid species have been studied thoroughly. It has been observed that, αβ-unsaturated mono/bis ketones, mono/bis esters and diazo carbonyl compounds yield dihydrofuran derivatives via [1,5]-electrocyclic ring closure and dihydrobenzoxepine derivatives via [1,7]-electrocyclic ring closure in the presence of Cu (acac)2 catalyst. The prior aim of this thesis is the synthesis of m-nitro benzylidene ethyl acetoacetate, p-nitro benzylidene acetylacetone, furylidene acetylacetone, furylidene ethyl acetoacetate, and furylidene methyl acetoacetate called α, β-unsaturated bis-carbonyl compounds. There are bis-methyl keton, bis-methyl keton/ethyl esther, bis-methyl keton/methyl esther functions in the biscarbonyl compounds which are planned to be synthesized. Besides, ethly crotonate synthesis has also been planned so that it is the smallest model of α, β- unsaturated monocarbonyl compounds which cannot polymerize. The structures of α, β-unsaturated bis-carbonyl compounds and mono-carbonyl compound have been clearly explained by 1H-NMR spectrums and GC-MS analysis. Afterwards, by using the α, β-unsaturated mono/bis carbonyl compounds which have been successfully synthesized, the research of Cu(acac)2 catalyzed ethylaceto diazoacetate (eada) decomposition reactions have been targetted.
In the research conducted by Olcay Anaç and her group, formal electrocyclization reactions of ylides derived from αβ-unsaturated carbonyl compounds and metallo carbenoid species have been studied thoroughly. It has been observed that, αβ-unsaturated mono/bis ketones, mono/bis esters and diazo carbonyl compounds yield dihydrofuran derivatives via [1,5]-electrocyclic ring closure and dihydrobenzoxepine derivatives via [1,7]-electrocyclic ring closure in the presence of Cu (acac)2 catalyst. The prior aim of this thesis is the synthesis of m-nitro benzylidene ethyl acetoacetate, p-nitro benzylidene acetylacetone, furylidene acetylacetone, furylidene ethyl acetoacetate, and furylidene methyl acetoacetate called α, β-unsaturated bis-carbonyl compounds. There are bis-methyl keton, bis-methyl keton/ethyl esther, bis-methyl keton/methyl esther functions in the biscarbonyl compounds which are planned to be synthesized. Besides, ethly crotonate synthesis has also been planned so that it is the smallest model of α, β- unsaturated monocarbonyl compounds which cannot polymerize. The structures of α, β-unsaturated bis-carbonyl compounds and mono-carbonyl compound have been clearly explained by 1H-NMR spectrums and GC-MS analysis. Afterwards, by using the α, β-unsaturated mono/bis carbonyl compounds which have been successfully synthesized, the research of Cu(acac)2 catalyzed ethylaceto diazoacetate (eada) decomposition reactions have been targetted.
Açıklama
Tez (Yüksek Lisans) -- İstanbul Teknik Üniversitesi, Fen Bilimleri Enstitüsü, 2010
Thesis (M.Sc.) -- İstanbul Technical University, Institute of Science and Technology, 2010
Thesis (M.Sc.) -- İstanbul Technical University, Institute of Science and Technology, 2010
Anahtar kelimeler
Karbonil bileşikleri,
diazo bileşikleri,
karbenoid,
elektrosiklik,
Carbonyl compounds,
diazo compounds,
carbenoid,
electrocyclic