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Reverse Cope Elimination of Hydroxylamines and Alkenes or Alkynes: Theoretical Investigation of Tether Length and Substituent Effects

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School of Chemistry, University of Melbourne, VIC 3010, Australia and Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology
§ Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
GlaxoSmithKline, Gunnels Wood Road, Stevenage Herts SG1 2NY, U.K.
CSIRO Materials Science and Engineering, Bag 10, Clayton South, VIC 3169, Australia
# Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
Cite this: J. Am. Chem. Soc. 2012, 134, 4, 2434–2441
Publication Date (Web):January 17, 2012
https://doi.org/10.1021/ja211568k
Copyright © 2012 American Chemical Society

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    Abstract

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    Quantum mechanical calculations have been used to study the intramolecular additions of hydroxylamines to alkenes and alkynes (“reverse Cope eliminations”). In intermolecular reverse Cope eliminations, alkynes are more reactive than alkenes. However, competition experiments have shown that tethering the hydroxylamine to the alkene or alkyne can reverse the reactivity order from that normally observed. The exact outcome depends on the length of the tether. In agreement with experiment, a range of density functional theory methods and CBS-QB3 calculations predict that the activation energies for intramolecular reverse Cope eliminations follow the order 6-exo-dig < 5-exo-trig < 5-exo-dig ≈ 7-exo-dig. The order of the barriers for the 5-, 6-, and 7-exo-dig reactions of alkynes arises mainly from differences in tether strain in the transition states (TSs), but is also influenced by the TS interaction between the hydroxylamine and alkyne. Cyclization onto an alkene in the 5-exo-trig fashion incurs slightly less tether strain than a 6-exo-dig alkyne cyclization, but its activation energy is higher because the hydroxylamine fragment must distort more before the TS is reached. If the alkene terminus is substituted with two methyl groups, the barrier becomes so much higher that it is also disfavored compared to the 5- and 7-exo-dig cyclizations.

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    Calculated geometries and energies, and complete refs 26 and 27. This material is available free of charge via the Internet at http://pubs.acs.org.

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