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605034 
Journal Article 
Oxidation reactions of some natural volatile aromatic compounds: anethole and eugenol 
Elgendy, EM; Khayyat, SA 
2008 
1 
Russian Journal of Organic Chemistry
ISSN: 1070-4280
EISSN: 1608-3393 
44 
6 
823-829 
English 
WOS:000257584500007 
trans-Anethole [1-methoxy-4-( trans-prop-1-en-1-yl)benzene] was isolated from anise seed oil ( Pimpinella anisum). Its photochemical oxidation with hydrogen peroxide gave the corresponding epoxy derivative together with 4-methoxybenzaldehyde. The thermal oxidation of trans-anethole with 3-chloroperoxybenzoic acid at room temperature resulted in the formation of dimeric epoxide, 2,5-bis(4-methoxyphenyl)-3,6-dimethyl-1,4-dioxane, as the only product. Photochemical oxygenation of trans-anethole in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll as sensitizer led to a mixture of 1-(4-methoxyphenyl)prop-2-en-1-yl hydroperoxide and 4-methoxybenzaldehyde. Eugenol was isolated from clove oil [ Eugenia caryophyllus (Spreng.)]. It was converted into 2-methoxy-4-(prop-2-en-1-yl)phenyl hydroperoxide by oxidation with hydrogen peroxide under irradiation. Thermal oxidation of eugenol with 3-chloroperoxypenzoic acid at room temperature produced 2-methoxy-4-(oxiran-2-ylmethyl)phenol, while sensitized photochemical oxygenation (in the presence of Rose Bengal or chlorophyll) gave 4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl)cyclohexa-2,5-dien-1-one. [ABSTRACT FROM AUTHOR] Copyright of Russian Journal of Organic Chemistry is the property of Springer Science & Business Media B.V. and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts) 
OXIDATION; AROMATIC compounds; ANISE; HYDROGEN peroxide; DIOXANE; ROSE bengal; CHLOROPHYLL 
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