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Molecules 2010, 15(7), 5012-5030; doi:10.3390/molecules15075012

Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation

Chromatography Laboratory, CIBIMOL, Research Center of Excellence CENIVAM, Building 45, Universidad Industrial de Santander, Carrera 27 calle 9, Bucaramanga, Colombia
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Received: 21 May 2010 / Revised: 21 June 2010 / Accepted: 25 June 2010 / Published: 22 July 2010
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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 trans-anethole; photoisomerization; HY zeolite; cis-anethole; dimerization
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MDPI and ACS Style

Castro, H.T.; Martínez, J.R.; Stashenko, E. Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation. Molecules 2010, 15, 5012-5030.

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