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Oxidation of o-Methoxyphenols with a Hypervalent Iodine Reagent: Improved Synthesis of Asatone and Demethoxyasatone (1999)

Kürti, László ; Szilágyi, László ; Antus, Sándor ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 2579-2581

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ISSN: 1434-193X

Keywords: Hypervalent iodine ; Phenols ; Oxidation ; Cyclohexa-2,4-dienones ; Dimerization ; Asatone ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4c-f, which dimerized spontaneously to a single product (5c-f) in each case. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol derivatives 1a and 1b, respectively.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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