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Molecules 2013, 18(10), 12820-12844; doi:10.3390/molecules181012820

Synthesis of Cycloveratrylene Macrocycles and Benzyl Oligomers Catalysed by Bentonite under Microwave/Infrared and Solvent-Free Conditions

1
Departamento de Ciencias Químicas, Campo 1, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Av 1o de Mayo s/n, Sta. Ma Las Torres, Cuautitlán Izcalli 54740, Estado de México, Mexico
2
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México, D.F., Mexico
*
Authors to whom correspondence should be addressed.
Received: 25 August 2013 / Revised: 11 October 2013 / Accepted: 11 October 2013 / Published: 16 October 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Tonsil Actisil FF, which is a commercial bentonitic clay, promotes the formation of cycloveratrylene macrocycles and benzyl oligomers from the corresponding benzyl alcohols in good yields under microwave heating and infrared irradiation in the absence of solvent in both cases. The catalytic reaction is sensitive to the type of substituent on the aromatic ring. Thus, when benzyl alcohol was substituted with a methylenedioxy, two methoxy or three methoxy groups, a cyclooligomerisation process was induced. Unsubstituted, methyl and methoxy benzyl alcohols yielded linear oligomers. In addition, computational chemistry calculations were performed to establish a validated mechanistic pathway to explain the growth of the obtained linear oligomers.
Keywords: bentonitic clay; solvent-free; microwave-assisted; infrared irradiation; cycloveratrylene bentonitic clay; solvent-free; microwave-assisted; infrared irradiation; cycloveratrylene
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

Miranda, R.; Valencia-Vázquez, O.; Maya-Vega, C.A.; Nicolás-Vázquez, I.; Vargas-Rodriguez, Y.M.; Morales-Serna, J.A.; García-Ríos, E.; Salmón, M. Synthesis of Cycloveratrylene Macrocycles and Benzyl Oligomers Catalysed by Bentonite under Microwave/Infrared and Solvent-Free Conditions. Molecules 2013, 18, 12820-12844.

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