title: Ring strain and its effect on the rate of the general-base catalyzed enolization of cyclobutanone.
abstract: [reaction: see text] The 3-quinuclidinone-catalyzed (pK(BH) = 7.5) enolization of cyclobutanone (1) in D(2)O at 25 degrees C, I = 1.0 (KCl) was followed by deuterium incorporation, which was determined by (1)H NMR. The second-order rate constant for the buffer-catalyzed deprotonation of 1 was found to be k(B) = 3.3 x 10(-4) M(-1) s(-1), which is compared to rates for acetone and 2-(2'-oxopropyl)benzaldehyde under similar conditions. The data shows that ring strain has very little effect on the energy barrier to deprotonation of 1 vs the unstrained systems.
authors.affiliation: Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA.
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Cantlin
authors.forename: James
authors.initials: J
authors.lastname: Drake
authors.forename: Richard W
authors.initials: RW
authors.lastname: Nagorski