THE ADDITION-REACTION OF DIALKYL CARBONATES TO KETONES

Citation
M. Selva et al., THE ADDITION-REACTION OF DIALKYL CARBONATES TO KETONES, Gazzetta chimica italiana, 123(9), 1993, pp. 515-518
Citations number
16
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0016-5603
Volume
123
Issue
9
Year of publication
1993
Pages
515 - 518
Database
ISI
SICI code
0016-5603(1993)123:9<515:TAODCT>2.0.ZU;2-R
Abstract
The reaction of benzyl phenyl ketone with dimethyl carbonate gives met hyl benzoate and methyl phenylacetate; diethyl carbonate gives the cor responding ethyl esters. The reaction takes place at high temperature (about 200-degrees-C) and in the presence of potassium carbonate as a catalyst. Other benzyl ketones react similarly. Aliphatic ketones yiel d a less selective addition. Accordingly, cyclohexanone with dimethyl carbonate gives dimethyl pimelate. The reaction is a retro-Claisen con densation, which occurs through the intermediate formation of the alko xycarbonyl derivative.