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. BertoliniPrimo
;R. AppianiSecondo
;M. PallaviciniPenultimo
;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.File | Dimensione | Formato | |
---|---|---|---|
revised.pdf
Open Access dal 06/11/2022
Tipologia:
Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione
741.94 kB
Formato
Adobe PDF
|
741.94 kB | Adobe PDF | Visualizza/Apri |
acs.joc.1c01469.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
651.71 kB
Formato
Adobe PDF
|
651.71 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.