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

abstract

  • 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.

author list (cited authors)

  • Singleton, D. A., Merrigan, S. R., & Thomas, A. A.

citation count

  • 7

publication date

  • January 1999