CHED Irvin Levy, Carmen Gauthier, Nicole Snyder  Monday, April 08, 2013 

1028 - Exploration of tandem sulfoxide-sulfenate rearrangement/intramolecular Diels-Alder reactions of 1,2,4-triazines

Louis J. Trzepkowski,, Larry G. French. Department of Chemistry, St. Lawrence University, Canton, NY 13617, United States

The Diels-Alder cycloaddition is one of the most powerful and widely exploited reactions in organic synthesis. This work attempts to develop a tandem 2,3-sigmatropic shift/intramolecular Diels-Alder cycloaddition of 1,2,4-triazines substituted at the 3-position with allyl, propargyl and allenyl sulfoxides. A sulfoxide to sulfenate rearrangement would lengthen the tether by one atom, facilitating intramolecular 4+2 cycloaddition. Extrusion of N2 would afford either directly, or upon oxidation, pyridine products.

Monday, April 8, 2013 12:00 PM
Undergraduate Research Posters (12:00 PM - 02:30 PM)
Location: Morial Convention Center
Room: Hall D


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