The Importance of the Ene Reaction for the C2−C6 Cyclization of Enyne−Allenes
- 18 May 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (23) , 5557-5562
- https://doi.org/10.1021/ja010346p
Abstract
The present study establishes the ene reaction as a competing reaction mechanism to the diradical mechanism for the thermal C2−C6 cyclization of enyne−allenes which possess bulky substituents at the alkyne terminus. Both reaction routes are found to possess nearly equal free energies of activation. As shown by our computations, primary H/D isotope effects could be used for a definite decision about the mechanism. Concerning the regioselectivity of the cyclization reactions of enyne−allenes our study resolves a long-standing deviation between theoretical results and experimental findings.This publication has 28 references indexed in Scilit:
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