Vinylcyclopropane oxygenation. Ab initio transition state analysis of 5-hexenylperoxy radical cyclization

C. K. Weinreb, D. Hartsough, Ken S. Feldman

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Abstract

Structure and energy calculations at the MP2/6-31G*//UHF/6-31G* level of four transition states for the cyclization of the 3-methyl-, and independently, the 3-fluoro-5-hexenylperoxy radical have been recorded. These calculations indicate that while the methyl substituent prefers to adopt an equatorial disposition on a chair-like transition state construct, the fluorine atom exhibits a strong preference for an axial alignment on the chair-like species. Boat-like transition states are significantly less favored than the chair-like alternatives, in contrast to the results of similar calculations in the all carbon (i.e., 5-hexenyl radical) cyclizations.

Original languageEnglish (US)
Pages (from-to)6859-6862
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number38
DOIs
Publication statusPublished - Sep 21 1995

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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