Deantiaromatization as a driving force in an electrocyclic reaction

ORGN 194

Michael Harmata, harmatam@missouri.edu1, Pinguan Zheng, pzk95@mizzou.edu1, Peter R. Schreiner, prs@org.chemie.uni-giessen.de2, and Armando Navarro-Vázquez, qoajnv@usc.es3. (1) Department of Chemistry, University of Missouri-Columbia, 601 S. College Avenue, Columbia, MO 65211, (2) Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, Giessen, 35392, Germany, (3) Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidade de Santiago de Compostela, Facultade de Química, Santiago de Compostela, 15782, Spain
As part of a program to explore the range of reactions that can be driven by loss of antiaromaticity, we have examined an electrocyclic ring closure of cyclopentadienenones. For the generation of the cyclopentadienones, we used a procedure that presumably produced the reactive intermediate relatively slowly, to avoid competing, intermolecular dimerization reactions. Computational analysis of the process suggested that the reaction took place through a pericyclic process and that deantiaromatization contributed a significant driving force.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006