The regioselectivity of acid-catalyzed epoxide ring-opening depends on carbocation stability
the verdict
SUPPORTED
the evidence backs this
confidence 77/100
The regioselectivity of acid-catalyzed epoxide ring-opening reactions and rearrangements is predominantly governed by the stability of the developing carbocation intermediate at the more substituted carbon.
Evidence for · 2
Lewis Acid-Catalyzed Alkylation of Azulene Derivatives with Epoxides and Oxetanes: A Regioselective Approach to Functionalized Azulene Alcohols.
2025 · cited by 1
Paper [6] notes that Lewis acid-catalyzed ring-opening of epoxides proceeds with high regioselectivity favoring nucleophilic attack at the more substituted position, consistent with carbocation stability in unsymmetrical systems.
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More for · 1
Radical Rearrangement of Terminal Epoxides to Methyl Ketones via Cobalt Photocatalysis.
2026 · cited by 0
Paper [7] explicitly states that the acid-catalyzed Meinwald rearrangement of epoxides is dominated by carbocation stability in determining regioselectivity.