Computational analysis of the dual reactivity of conjugated hetero-'ene-ene-yne' systems

ORGN 409

Sean P. McClintock, smcclint@uoregon.edu1, Laura D. Shirtcliff, lshirt@uoregon.edu1, Rainer Herges, rherges@oc.uni-kiel.de2, and Michael M. Haley, haley@uoregon.edu1. (1) Department of Chemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, (2) Institut f. Organische Chemie, Universität Kiel, Otto-Hahn Platz 4, Kiel, D-24098, Germany
There is considerable interest in the synthesis of heterocyclic compounds derived from hetero-‘ene-ene-yne' precursors. The ring forming reactions often follow unusual reaction mechanisms and afford hard to obtain substitution patterns. Work in our lab with azo-ene-yne compounds has examined the dual reactivity of these systems to yield either five- or six-membered heterocycles. Recent work has included addition of nitroso and nitrile moieties into the scaffolds. This paper extends our computational investigations by examining a new series of hetero-‘ene-ene-yne' and all-carbon ‘ene-ene-yne' precursor systems for potential experimental study.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008