title: Synthesis of cycloveratrylene macrocycles and benzyl oligomers catalysed by bentonite under microwave/infrared and solvent-free conditions.
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.
authors.affiliation: 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. mirruv@yahoo.com.mx.
authors.forename: René
authors.initials: R
authors.lastname: Miranda
authors.forename: Omar
authors.initials: O
authors.lastname: Valencia-Vázquez
authors.forename: Carlos Abel
authors.initials: CA
authors.lastname: Maya-Vega
authors.forename: Inés
authors.initials: I
authors.lastname: Nicolás-Vázquez
authors.forename: Yolanda Marina
authors.initials: YM
authors.lastname: Vargas-Rodriguez
authors.forename: José Antonio
authors.initials: JA
authors.lastname: Morales-Serna
authors.forename: Eréndira
authors.initials: E
authors.lastname: García-Ríos
authors.forename: Manuel
authors.initials: M
authors.lastname: Salmón
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D001546:Bentonite / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis; D002384:Catalysis; D003198:Computer Simulation; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D011108:Polymers / Q000138:chemical synthesis; D011789:Quantum Theory; D012997:Solvents; D013816:Thermodynamics
chemical_list: D000475:Alkenes; D001593:Benzyl Compounds; D047028:Macrocyclic Compounds; D011108:Polymers; D012997:Solvents; D001546:Bentonite