The Retro-Nazarov Reaction
- 9 November 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (48) , 14328-14329
- https://doi.org/10.1021/ja028729q
Abstract
Treatment of 2-bromo-4-t-butoxy-2-cyclopentenone with an amine base in refluxing trifluoroethanol afforded a ring-opened product in moderate yield. The mechanism of the reaction has been formulated as a retro-Nazarov reaction in which an oxyallylic cation undergoes ring-opening to a dienone. Several other examples of the reaction have been established through a protocol involving the conjugate addition of an organocuprate to 2-bromo-4-t-butoxy-2-cyclopentenone followed by treatment of the adducts with base in refluxing trifluoroethanol.Keywords
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