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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

1,* , 1, 2
, 3
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 and 1,*
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   montmorillonite clay; oligomerization; antrhacene; EPR; radical cation  
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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