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Updated: Aug 7, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enolate structure and electron affinity
David A Walthall1, Joel M Karty, Bettina Römer
1Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.
Abstract:
Photodetachment cross sections for a series of cyclic enolates were measured using a continuous wave (CW) ion cyclotron resonance instrument to generate and detect the ions. We report electron affinities for the radicals corresponding to the removal of the extra electron from the following anions: 2-methylcyclopent-1-enolate, 3-methylcyclopent-1-enolate, 4-methylcyclopent-1-enolate, 5-methylcyclopent-1-enolate, 2-methylcyclohex-1-enolate, 3-methylcyclohex-1-enolate, 4-methylcyclohex-1-enolate, 4-ethylcyclohex-1-enolate, 5-methylcyclohex-1-enolate, and 6-methylcyclohex-1-enolate. Some of these anions are mixed with their tautomers, derived from deprotonation of the parent ketone; the consequences of this are analyzed. The effect of alkylation on the electron affinities is discussed. The effect of vibrational modes on the lifetimes of the dipole-bound states of 4-methylcyclohex-1-enolate and 4-ethylcyclohex-1-enolate is discussed.
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