Anethole isomerization and dimerization induced by acid sites or UV irradiation.
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.
Castro
Hans T
HT
Chromatography Laboratory, CIBIMOL, Research Center of Excellence CENIVAM, Building 45, Universidad Industrial de Santander, Carrera 27 calle 9, Bucaramanga, Colombia.
Martínez
Jairo René
JR
Stashenko
Elena
E
D000143:Acids / Q000737:chemistry; D000475:Alkenes; D000081248:Allylbenzene Derivatives; D000840:Anisoles / Q000737:chemistry* / Q000528:radiation effects*; D003503:Cyclobutanes; D019281:Dimerization; D005421:Flavoring Agents; D007536:Isomerism; D017640:Silicates / Q000737:chemistry; D014466:Ultraviolet Rays
D000143:Acids; D000475:Alkenes; D000081248:Allylbenzene Derivatives; D000840:Anisoles; D003503:Cyclobutanes; D005421:Flavoring Agents; D017640:Silicates; C117224:1-hexene; C006578:anethole