Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones

 
 
 
 

Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones

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Title: Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones
Author: Katkova, Olga A
Description: Nitrones have been known for some time as quite versatile intermediates in organic synthesis. They have been employed for stereoselective formation of synthetically useful isoxazolidines by their 1,3-dipolar cycloaddition reactions with alkenes. We have further investigated the behavior of some non-conjugated and conjugated nitrones in cycloaddition reactions. Several α nitrones were synthesized and characterized. New reactions with electron-rich butylvinylethers were studied. All the synthesized nitrones were shown to undergo 1,3 dipolar cycloaddition with formation of 4- and 5-substituted isoxazolidines. We successfully synthesized a trans-chelating tridentate ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) and converted it to the cationic aqua complex Ni(ClO 4 ) 2 *PhDBFOX. This complex was previously described by Kanemasa ^47 as the most selective chiral catalyst for the normal electron-demand 1,3-dipolar cycloaddition reaction between nitrones and alkenes. We studied the effect of this catalyst on reactivity of α and α A separate study of the photolysis of these non-conjugated and conjugated nitrones proved the formation of oxaziridines. The structure of these 3-membered ring nitrone isomers was established by NMR analysis. Oxidation of oxaziridines with peroxides was briefly investigated.
Permanent Link: http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1123003688
http://hdl.handle.net/2374.OX/15565
Date: 2005

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