2,3-distibstitüebenzobarrelenlerin yeni ve uygun bir metodla sentezi ve 2,3-dimetoksibenzobarrelenin fotooksijenasyonu
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- Tez No: 355005
- Danışmanlar: PROF. DR. METİN BALCI
- Tez Türü: Yüksek Lisans
- Konular: Kimya, Chemistry
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 1989
- Dil: Türkçe
- Üniversite: Atatürk Üniversitesi
- Enstitü: Fen Bilimleri Enstitüsü
- Ana Bilim Dalı: Kimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 79
Özet
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Özet (Çeviri)
This study involves the synthesis of the disubstitue benzobarrelenes with a high yield and an available \Olay. T~erefore dicyanobenzobarrelene(57) was synthesized from the reaction of the 2, 3-dibromobenzobarrelene (64) \'1i th CuCN. After BuLi was added to dibromobenzobarreli?ne its derivative containing methylbromo(65) was syn'thesized with CH3 I. Methylcyano derivative(66) was obtained reaction of this compound(65) with CuCN. After BuLi and CO2 were added to dibromobenzobarrelene(64) and its derivative with methylbromo(65) , their derivatives with bromoacid(68) and methylacid(67) were synthesized. 'rhe derivative with bromoacid (68) was reacted wi th diazomethane and Vias converted to ,the it:' ester derivative(69) . Dimethoxybenzobarrelene (72) was obtained from tl1e reaction of the dibromobenzobarrelene(64) with CuI and sodium methoxide. It was seen that the photooxygene'tion of the dimethoxybenzobarrelene gave exo-dioxetane (86), endo-dioxetane( 87) and cis-l,4-dicarbomethoxy-I,4-dihydronaphtalene (89). These dioxetanes could not be isolated because they are high unstable and are easily decomposed to the compound (88) on heating Vie expected that the reaction of this compound \'Ii th CoTPP sensi ti zed could give the compound (89) but the spectroscopic data indicated that ti1e compound(89) was not occured, this reaction gave only the compound (88) . 1, 4-dicarbomethoxynaphtalene (96) Vias obtained from the reaction of DDQ and dihydronaphtalene(88) .
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