Lewis acid catalyzed 1,3-dipolar cycloadditon reactions of stabilized azomethine ylides

Doğan, Özdemir
Diethylzinc was tested for the first time as the Lewis acid in 1,3-dipolar cycloaddition reactions of azomethine ylides to synthesize pyrrolidine derivatives. A new, easily applicable and highly selective method was developed for the synthesis of highly substituted pyrrolidines. By the application of this method, the synthesis of three new pyrrolidine derivatives was achieved.


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ÇALIŞKAN, Raşit; Sari, Ozlem; Balcı, Metin (Wiley, 2017-09-01)
3-Chloro-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)-3-hydroxy-5,5-dimethylcy-clohex- 2-en-1-one, synthesized by the reaction of oxabenzonorbornadiene with Mn(OAc)(3) and dimedone in the presence of HCl in acetic acid, was submitted to ring-opening reactions with BBr3 and H2SO4. Reaction with BBr3 yielded 2 products, a 5-membered ring and an 8-membered ring, with the former being the major product. However, the H2SO4-supported reaction exclusively formed an 8-membered ring. The mechanism of formation of th...
Diethylzinc mediated 1 3 dipolar cycloaddition reaction of chiral azomethine ylides asymmetric synthesis of ferrocenyl substituted pyrrolidine derivatives
Doğan, Özdemir; DİNÇER, Ülkü; ARICI, Cengiz (2002-10-01)
Asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives was successfully achieved by diethylzinc-mediated 1,3-dipolar cycloaddition reactions of chiral azomethine ylides with a number of electron-deficient dipolarophiles. Chiral azomethine ylides were formed by condensing glycyl sultam with ferrocenecarboxaldehyde via imine tautomerization and complexation with diethylzinc. All of the cycloaddition reactions gave ferrocenyl-substituted pyrrolidine derivatives with very high regio- and diaster...
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Michael addition reactions as an efficient method for carbon-carbon bond formations have been intensively explored in the context of enantioselective organocatalysis using aldehydes, ketones, 1,3- dicarbonyl compounds and nitroalkenes as donors. However, there are very few studies using thiol derivative as a nucleophile. In this thesis, enantioselective Michael addition reaction of thioacetic acid as Michael donor and 10 trans-β-nitrostyrene derivatives as Michael acceptors have been studied. The products o...
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Kurnaz, Emine; Önal, Işık; Department of Chemical Engineering (2011)
Propylene epoxidation reaction was investigated on catalytic surfaces of chlorinated copper(I) oxide and ruthenium(IV) oxide using periodic density functional theory (DFT). Cu2O(001) and (110) surface of RuO2 was selected to generate chlorinated surfaces to be used in the study. Besides epoxidation, other reactions that compete with epoxidation were also studied such as formations of allyl-radical, acrolein, acetone on chlorinated Cu2O(001) and formations of propionaldehyde, allyl-radical and acetone on chl...
Conductimetric and potentiometric titration of some hydroxylated cinnamic acids with tetrabutylammonium hydroxide in non-aqueous media
Aktas, AH; Yasar, G; Alsancak, O; Demirci, S (2001-01-01)
In this study, four hydroxycinnamic acids, namely 3,4-dihydroxycinnamic acid, 4-hydroxycinnamic acid, 4-hydroxy -3- methoxycinnamic acid and 4-hydroxy-3,5-dimethoxycinnamic acid, were titrated conductimetrically and potentiometrically using triethylamine and tetrabutylammonium hydroxide in acetonitrile, 2-propanol, and pyridine solvents under a nitrogen atmosphere at 25 degreesC.
Citation Formats
Ö. Doğan and Ü. KANIŞKAN, “Lewis acid catalyzed 1,3-dipolar cycloadditon reactions of stabilized azomethine ylides,” TURKISH JOURNAL OF CHEMISTRY, pp. 365–371, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/53923.