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Molecules ; 18(10): 12820-44, 2013 Oct 16.
Article in English | MEDLINE | ID: mdl-24135939

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.


Subject(s)
Bentonite/chemistry , Macrocyclic Compounds/chemical synthesis , Alkenes/chemical synthesis , Benzyl Compounds/chemical synthesis , Catalysis , Computer Simulation , Macrocyclic Compounds/chemistry , Microwaves , Models, Chemical , Models, Molecular , Molecular Conformation , Polymers/chemical synthesis , Quantum Theory , Solvents , Thermodynamics
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