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The Effect Of Variation Of N-Substituents On Oxidopyridinium Ions In (4+3) Cycloadditions, Zahria Patrick, Madison Clark
The Effect Of Variation Of N-Substituents On Oxidopyridinium Ions In (4+3) Cycloadditions, Zahria Patrick, Madison Clark
Undergraduate Research Symposium
The aim of this research project is to expand the scope of 4 + 3 cycloadduct chemistry by varying functional groups attached to the prerequisite oxidopyridinium ion for each respective cycloadduct product. While N-substitution of the pyridinium precursor is known to proceed smoothly if alkylated by a lone methyl group, we evaluated the effect a larger alkyl group would have on the overall yield of the 4 + 3 cycloadduct product.
Isobutyl triflate, generated from the known reaction between isobutyl alcohol and triflic anhydride, was reacted with ethyl 5-hydroxy-nicotinate to generate the respective N-isobutyl oxidopyridinium ion in quantitative …