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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; in revised form: 21 June 2010 / Accepted: 25 June 2010 / Published: 22 July 2010
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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Castro, H.T.; Martínez, J.R.; Stashenko, E. Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation. Molecules 2010, 15, 5012-5030.
Castro HT, Martínez JR, Stashenko E. Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation. Molecules. 2010; 15(7):5012-5030.
Castro, Hans T.; Martínez, Jairo René; Stashenko, Elena. 2010. "Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation." Molecules 15, no. 7: 5012-5030.