Molecules 2010, 15(11), 8156-8168; doi:10.3390/molecules15118156
Article

Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study

José Antonio Morales-Serna 1,* email, Luis E. López-Duran 1 , Miguel Castro 2 email, Luis E. Sansores 3 email, Mikhail Zolotukhin 3 email and Manuel Salmón 1,* email
1 Instituto de Química de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria Coyoacán 04510, México, D.F., Mexico 2 Facultad de Química de la Universidad Nacional Autónoma de México, Circuito Interior, Ciudad Universitaria Coyoacán 04510, México, D.F., Mexico 3 Instituto de Investigaciones en Materiales, de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria Coyoacán 04510, México, D.F., Mexico
* Authors to whom correspondence should be addressed.
Received: 8 August 2010; in revised form: 22 October 2010 / Accepted: 27 October 2010 / Published: 11 November 2010
(This article belongs to the Section Organic Synthesis)
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Abstract: Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10-dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7-tetramethylanthracene. It was also found that the compounds 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetra-methylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7-Tetramethylanthryl radical cation was formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene; it was characterized by Electronic Paramagnetic Resonance (EPR). On the other hand, a theoretical analysis was performed, allowing the rationalization of the observed products and some of the key reaction steps.
Keywords: montmorillonite clay; oligomerization; antrhacene; EPR; radical cation  

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MDPI and ACS Style

Morales-Serna, J.A.; López-Duran, L.E.; Castro, M.; Sansores, L.E.; Zolotukhin, M.; Salmón, M. Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study. Molecules 2010, 15, 8156-8168.

AMA Style

Morales-Serna JA, López-Duran LE, Castro M, Sansores LE, Zolotukhin M, Salmón M. Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study. Molecules. 2010; 15(11):8156-8168.

Chicago/Turabian Style

Morales-Serna, José Antonio; López-Duran, Luis E.; Castro, Miguel; Sansores, Luis E.; Zolotukhin, Mikhail; Salmón, Manuel. 2010. "Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study." Molecules 15, no. 11: 8156-8168.

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