Cyclic ketones were quickly and quantitatively converted to 5-, 6- and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and non-pollutant oxidizing reagent, in 1M NaH2PO4/Na2HPO4 water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed thus making unnecessary the adoption of more com-plex and non-ecofriendly procedures previously developed to avoid lactone hydrolysis. With some changes, the method was successfully applied also to water insoluble ketones such as adamantanone, acetophenone, 2-indanone and challenging cy-cloheptanone.

Green Oxidation of Ketones to Lactones with Oxone in Water / V. Bertolini, R. Appiani, M. Pallavicini, C. Bolchi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 86:21(2021), pp. 15712-15716. [10.1021/acs.joc.1c01469]

Green Oxidation of Ketones to Lactones with Oxone in Water

V. Bertolini
Primo
;
R. Appiani
Secondo
;
M. Pallavicini
Penultimo
;
C. Bolchi
Ultimo
2021

Abstract

Cyclic ketones were quickly and quantitatively converted to 5-, 6- and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and non-pollutant oxidizing reagent, in 1M NaH2PO4/Na2HPO4 water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed thus making unnecessary the adoption of more com-plex and non-ecofriendly procedures previously developed to avoid lactone hydrolysis. With some changes, the method was successfully applied also to water insoluble ketones such as adamantanone, acetophenone, 2-indanone and challenging cy-cloheptanone.
Settore CHIM/06 - Chimica Organica
Settore CHIM/08 - Chimica Farmaceutica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/882204
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