Journal of the American Chemical Society p. 1029 - 1040 (1984)
Update date:2022-08-28
Topics:
Baldwin
Black
The relative concentrations of stereoisomers in product mixtures were determined as a function of time by using a combination of analytical techniques: vapor phase chromatography, polarimetry, NMR spectroscopy, and NMR spectroscopy in the presence of an optically active lanthanide shift reagent. The stereochemical reaction kinetics reveal that the Smith mechanism is not a plausible model for one-center epimerization; two trimethylenes, produced through two distinct cyclopropane C-C bond cleavages, are implicated, since all three possible one-center epimerizations are seen.
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