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Transition structures, energetics, and nucleus-independent chemical shifts for divinylcyclobutene-to-cyclooctatriene rearrangement: A DFT study
Date
2004-02-06
Author
Zora, Metin
Metadata
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The minimum energy reaction paths and nucleus-independent chemical shifts (NICS) for the Cope rearrangement of cis-3,4-divinylcyclobutene, obtained by (U)B3LYP/6-31G* calculations, are reported. Three transition structures (endo-boatlike, chairlike, and exo-boatlike) have been located, giving rise to formation of cis,cis,cis-, cis,cis,trans-, and trans,cis, trans- 1, 3,5-cyclooctatrienes, respectively. The minimum energy path proceeds through an endo-boatlike, aromatic transition structure. The reaction path of the rearrangement is intervened by enantiomerization saddle point of the product. NICS values calculated for transition structures agree qualitatively with their activation energy and reaction exothermicity orders. Cope rearrangement and electrocyclic ring-opening processes of cis-3,4-divinylcyclobutene are competitive, but the former is relatively more favored and exothermic than the latter.
Subject Keywords
Organic Chemistry
URI
https://hdl.handle.net/11511/46924
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo0350209
Collections
Department of Chemistry, Article