CHED 849 |
| Joanna L. Schmidt, Colin Jennings, and David M. Birney. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061 |
| According to the pericyclic reaction rules, chemical reactions involving cyclic transition states can either be forbidden or allowed, depending on whether or not the transition state forms an aromatic ring. However, there is evidence to suggest that reactions involving non-aromatic transition states, known as psuedopericyclic reactions, can occur. For instance, in this experiment, cis-3-penten-2-ol acetate was synthesized, and subsequently eliminated using a multi-photon infrared laser. Results indicate an eight-centered transition state from elimination, which should be forbidden according to the pericyclic reaction rules. Also attempted was the elimination of the corresponding xanthate ester and a benzyl-xanthate-ester, to determine if the psuedopericyclic reaction can occur in the presence of sulfur instead of oxygen. Calculations have indicated that the xanthate esters will have lower reaction barriers along the psuedopericyclic reaction path. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |