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

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...

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Published inEuropean journal of organic chemistry Vol. 1999; no. 10; pp. 2579 - 2581
Main Authors Kürti, László, Szilágyi, László, Antus, Sándor, Nógrádi, Mihály
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.10.1999
WILEY‐VCH Verlag GmbH
Wiley
Subjects
4-dienones
Asatone
Chemistry
Chemistry, Organic
Cyclohexa-2
Cyclohexa‐2,4‐dienones
Dimerization
Hypervalent iodine
Oxidation
Phenols
Physical Sciences
Science & Technology
hypervalent iodine
phenols
SPECTROSCOPY
asatone
oxidation
dimerization
SENSITIVITY
CYCLODEHYDROGENATION
2'-HYDROXYCHALCONES
DIACETATE
cyclohexa-2,4-dienones
FLAVONES
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Summary: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.
Bibliography:ArticleID:EJOC2579
ark:/67375/WNG-F70QPQQ7-N
istex:9163A38F53A3EFB81BCA3A8E7BBC7755839DCFEC
ISSN:1434-193X
1099-0690
DOI:10.1002/(SICI)1099-0690(199910)1999:10<2579::AID-EJOC2579>3.0.CO;2-H