Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

Daniel A. Singleton, Steven R. Merrigan, Allen A. Thomas

Research output: Contribution to journalArticle

9 Scopus citations


The variation in cis versus trans deuterium content in natural-abundance ethyl vinyl ether is retained in its cycloadduct with hexachloroeyclopentadiene, indicative of a stereospecific process. The kinetic isotope effects for this reaction were also determined at natural abundance, and suggest a very asynchronous but concerted process. This conclusion is backed by comparison with theoretically calculated isotope effects.

Original languageEnglish (US)
Pages (from-to)639-642
Number of pages4
JournalTetrahedron Letters
Issue number4
Publication statusPublished - Jan 22 1999


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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