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Reactions of paulownin, gmelinol and gummadiol with 2,5-dichloro-5,6-dicyanobenzoquinone.

โœ Scribed by R.S. Ward; A. Pelter; I.R. Jack; P. Satyanarayana; B.V.Gopala Rao; P. Subrahmanyam

Book ID
104234411
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
175 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Paulownin and gmelinol react with DDQ to give 4-pyrone derivatives. Gummadiol reacts under the same conditions to give a pyrone aldehyde and an unsaturated y-lactone. 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) has been previously shown to react with lignans of the monoarylidene-butyrolactone and aryl-tetralin series. 1,2 We have now studied the reactions of this reagent with paulownin (L),3-5 gmelinol (z)5-7 and gummadiol (3),8,g three lignans belonging to the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane series. 10

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โœ Shigeyasu Kuroda; Makoto Funamizu; Yoshio Kitahara; Toyonobu Asao ๐Ÿ“‚ Article ๐Ÿ“… 1975 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 107 KB

2,3-Dichloro-5,6-dicyanobenzoquinone (004) is well known useful oxidizing reagent in organic synthesis and has powerful ability in complex formation with unsaturated compounds.L However, only one report on the cycloaddition of DDQ has appeared,3 in spite of p-benzoquinone