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• Martínez, J
• Stashenko, E
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Molecules 2010, 15(7), 5012-5030; doi:10.3390/molecules15075012

Article

Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation

Hans T. Castro, Jairo René Martínez*  and Elena Stashenko

Chromatography Laboratory, CIBIMOL, Research Center of Excellence CENIVAM, Building 45, Universidad Industrial de Santander, Carrera 27 calle 9, Bucaramanga, Colombia

* Author to whom correspondence should be addressed.

Received: 21 May 2010; in revised form: 21 June 2010 / Accepted: 25 June 2010 / Published: 22 July 2010

Download PDF Full-Text [429 KB, Updated Version, uploaded 29 July 2010 09:12 CEST]

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Abstract: The formation of cis-anethole and various dimers as a result of the exposure of trans-anethole to microporous solid acids (dealuminated HY zeolites), or UV-Vis irradiation was established by means of high resolution gas chromatography coupled to mass spectrometry. 3,4-bis-(4-Methoxyphenyl)-(E)-hex-2-ene was the most abundant compound among eight different methoxyphenyl-disubstituted hexenes produced by electrophilic addition and elimination reactions induced by HY zeolites. (1a,2a,3b,4b)-1,2-bis(4-Methoxyphenyl)-3,4-dimethylcyclobutane was the principal component in the mixture of 5 methoxyphenyl-disubstituted cyclobutanes found, together with cis-anethole, after UV-Vis irradiation of a trans-anethole solution in toluene.

Keywords: trans-anethole; photoisomerization; HY zeolite; cis-anethole; dimerization

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