OLEFIN-INSERTION REACTION BETWEEN THE CARBONYLS OF BENZILS - FORMATION OF 1,4-DIKETONES BY MICHAEL ADDITION CATALYZED BY CYANIDE ION

Authors
MIYASHITA A NUMATA A SUZUKI Y IWAMOTO K HIGASHINO T
Citation
A. Miyashita et al., OLEFIN-INSERTION REACTION BETWEEN THE CARBONYLS OF BENZILS - FORMATION OF 1,4-DIKETONES BY MICHAEL ADDITION CATALYZED BY CYANIDE ION, Chemistry Letters, (8), 1997, pp. 697-698
Citations number
9
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
8
Year of publication
1997
Pages
697 - 698
Database
ISI
SICI code
0366-7022(1997):8<697:ORBTCO>2.0.ZU;2-H
Abstract
Benzils (1) react with Michael addition accepters (2) in the presence of cyanide ion as a catalyst to give 1,4-diketones (3): which are prod ucts of ethylene group insertion between the carbonyls of the benzils. The 1,4-diketones (3) are produced through the formation of the O-aro ylmandelonitrile anion, followed by Michael addition and rearrangement of the aroyl group with decyanation.