Enolates in 3-D: An experimental and computational study of deprotonated 2-adamantanone

Matthew M. Meyer, Steven R Kass

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7 Scopus citations

Abstract

Deprotonation of 2-adamantanone (1) in the gas phase affords the corresponding β-enolate anion. This ion was independently prepared by the fluoride-induced desilylation of 4-trimethylsilyl-2-adamantanone, and its reactivity and thermodynamic properties were measured (ΔH° acid = 394.7 ± 1.4, EA = 16.8 ± 1.6, and BDE = 97.9 ± 2.1 kcal mol-1). Density functional theory calculations with B3LYP and M06-2X, and G3 energies are also reported. The computed relative stabilities of the conjugate bases of 1 are as follows: β > γ > α > δ. An attempt to prepare the γ-anion, however, resulted in the formation of its ring-opened isomer (i.e., deprotonated 7-methylenebicyclo[3.3.1]nonan-2-one).

Original languageEnglish (US)
Pages (from-to)4274-4279
Number of pages6
JournalJournal of Organic Chemistry
Volume75
Issue number12
DOIs
StatePublished - Jun 18 2010

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