Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones

 
 
 
 

Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones

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dc.contributor.advisor Kinstle, Thomas H en_US
dc.contributor.author Katkova, Olga A en_US
dc.date.accessioned 2008-07-08T18:33:47Z
dc.date.available 2008-07-08T18:33:47Z
dc.date.created 2005 en_US
dc.date.issued 2008-07-08T18:33:47Z
dc.identifier.uri http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1123003688 en_US
dc.identifier.uri http://hdl.handle.net/2374.OX/15565
dc.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. en_US
dc.format application/pdf en_US
dc.format 79p. en_US
dc.rights unrestricted en_US
dc.rights Copyright and permissions information available at the source archive en_US
dc.subject synthesis of nitrones en_US
dc.subject ptochemical reactions of nitrones en_US
dc.subject 1,3 Cycloaddition reactions of nitrones en_US
dc.title Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name MS en_US
dc.degree.level masters en_US
dc.degree.discipline Chemistry en_US
dc.degree.grantor Bowling Green State University en_US
dc.contributor.publisher Bowling Green State University / OhioLINK en_US

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