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

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

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 / Revised: 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   montmorillonite clay; oligomerization; antrhacene; EPR; radical cation  
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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