Applications of the Structure Correlation Principle to Pericyclic and Pseudopericyclic Fragmentation Reactions, Including the Retro Diels Alder and Retro Chelotropic Reactions

Jonathan M. White 1Yit Wooi Goh 1David Birney 2

1. The Univeristy of Melbourne (UNIMELB), Grattan Street, Melbourne 3052, Australia
2. Texas Tech University, Lubbock TX79409-1, United States

Abstract

Structural changes which occur during a chemical reaction can manifest in the ground state structure as deviations of bond distances and angles from 'normal values' along the reaction coordinate [1]. We have applied this principle to pericyclic fragmentations including the retro Diels Alder and retro Cheletropic reactions [2-4], by determining accurate low temperature X-ray crystal structures of selected model substrates. Qualitative structure reactivity relationships will be discussed, and the structural effects associated with asychronous reaction pathways will be discussed.

[1] J. Dunitz, X-Ray Analysis and the Structure of Organic Molecules, Cornell University Press Ltd., London, 1979.

[2] B. R. Pool, J. M. White, Org. Lett. 2000, 2, 3505.

[3] D. Birney, T. K. Lim, J. H. P. Koh, B. R. Pool, J. M. White, J. Am. Chem. Soc. 2002, 124, 5091.

[4] G. Y. Wooi, J. M. White, Org. Biomolec. Chem. 2005, 3, 972.

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Presentation: oral at 18th Conference on Physical Organic Chemistry, Symposium 2, by Jonathan M. White
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-01-10 00:17
Revised:   2009-06-07 00:44
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