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The deoxygenation of styrene oxide with dichlorocarbene is studied by a combination of isotope effects and theoretical calculations. A normal 13 C isotope effect of 1.016 is observed for the α-carbon of the styrene oxide but a surprising inverse isotope effect of 0.995 is observed at the β-carbon. This is indicative of a highly asynchronous process in which the C α –O bond is broken...
The fragmentation of an epoxy imino-1,3,4-oxadiazoline is studied by a combination of isotope effects and theoretical calculations. Significant primary 13 C isotope effects are observed at the two oxadiazoline carbons but negligible isotope effects are observed at the remaining carbons. This is consistent with a rate-limiting fragmentation of the oxadiazoline without fragmentation of the adjacent...
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