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Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones
Katkova, Olga A

2005, Master of Science (MS), Bowling Green State University, Chemistry.
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.
Thomas Kinstle (Advisor)
79 p.

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Katkova, O. (2005). Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones. (Electronic Thesis or Dissertation). Retrieved from https://etd.ohiolink.edu/

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Katkova, Olga. "Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones." Electronic Thesis or Dissertation. Bowling Green State University, 2005. OhioLINK Electronic Theses and Dissertations Center. 29 Aug 2015.

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Katkova, Olga "Photochemical Isomerization and Stereoselective Thermal Reactions of Conjugated Nitrones." Electronic Thesis or Dissertation. Bowling Green State University, 2005. https://etd.ohiolink.edu/

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