Benzocyclobutenone enolate: an anion with an antiaromatic resonance structure†

KM Broadus, SR Kass

Index: Broadus, Katherine M.; Kass, Steven R. Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 11 p. 2389 - 2396

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Citation Number: 14

Abstract

Benzocyclobutenone enolate (1a) was synthesized by deprotonating its conjugate acid with fluoride ion in the gas phase using a Fourier transform mass spectrometer. Reactions of 1a were explored and C-alkylation was found to be greatly preferred over oxygen attack. Thermodynamic properties (ΔH° acid (1)= 360.3±2.1 kcal mol–1, EA (benzocyclobutenyl radical)= 1.90±0.10 eV, and BDE (C–H)= 90.5±3.1 kcal mol–1) also were measured. The ...