Oxidation of o-methoxyphenols with a hypervalent iodine reagent: Improved synthesis of asatone and demethoxyasatone

Authors
Kurti, L Szilagyi, L Antus, S Nogradi, M
Citation
L. Kurti et al., Oxidation of o-methoxyphenols with a hypervalent iodine reagent: Improved synthesis of asatone and demethoxyasatone, EUR J ORG C, (10), 1999, pp. 2579-2581
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
10
Year of publication
1999
Pages
2579 - 2581
Database
ISI
SICI code
1434-193X(199910):10<2579:OOOWAH>2.0.ZU;2-4
Abstract
Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate ( PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4 c-f, which dimerized spontaneously to a single product (5c-f) in each ease. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol deri vatives 1a and 1b, respectively.