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A study on kinetic CH-acidity; The α-epimerization of β-lactones

✍ Scribed by Johann Mulzer; Matthias Zippel

Book ID
104241683
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
236 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

The rate constants of the O<-epimerization of the B-lactone 1 show a LFE-correlation with the solvent donicity parameters DN or B; additionally, the kinetic CH-acidity of 1 is unusually high. The enolization of carbonyl compounds has been a subject of intensive in-1 vestigation for many years . Among the various methods which have been used for studying this reaction kinetically are deuteriation, bromination,racemization and epimerization. Herein we report kinetic data on the o<-epimerization 2 of B-lactones. Model System and Kinetic Scheme Cis-4-tert-butyl-3-phenyl-2-oxetanone3 (I)proved to be a suitable model system (Scheme I). Scheme I

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