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