Oligomerization of 3,5-dimethyl benzyl alcohol promoted by clay: experimental and theoretical study.
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.
Instituto de Química de la Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, México, D.F., Mexico. morser@correo.unam.mx
José Antonio
JA
Morales-Serna
Luis E
LE
López-Duran
Miguel
M
Castro
Luis E
LE
Sansores
Mikhail
M
Zolotukhin
Manuel
M
Salmón
D001546:Bentonite / Q000737:chemistry*; D019905:Benzyl Alcohol / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D015394:Molecular Structure; D058105:Polymerization
D001546:Bentonite; D019905:Benzyl Alcohol