Isotope effects and the mechanism of deoxygenation of epoxides with dichlorocarbene
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The deoxygenation of styrene oxide with dichlorocarbene is studied by a combination of isotope effects and theoretical calculations. A normal 13C isotope effect of 1.016 is observed for the -carbon of the styrene oxide but a surprising inverse isotope effect of 0.995 is observed at the -carbon. This is indicative of a highly asynchronous process in which the C-O bond is broken without any progress in the breakage of C-O bond. Theoretical calculations support this interpretation. This coarctate reaction is formally concerted as it avoids involving a high-energy intermediate, but it appears uninfluenced by transition state aromaticity. 2005 Published by Elsevier Ltd.
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Singleton, D. A., & Wang, Z. H.
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