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Degree

Master of Science (MS), Bowling Green State University, Chemistry, 2005.

Abstract

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.

Subject Headings

Chemistry, Organic

Keywords

synthesis of nitrones; ptochemical reactions of nitrones; 1,3 Cycloaddition reactions of nitrones

Advisor

Thomas H Kinstle

Pages

79p.

Document number: bgsu1123003688
Permalink: http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1123003688

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