title: A Macrocyclic 1,4-Diketone Enables the Synthesis of a p-Phenylene Ring That Is More Strained than a Monomer Unit of [4]Cycloparaphenylene.
abstract: The synthesis of a p-terphenyl-based macrocycle, containing a p-phenylene unit with 42.6 kcal/mol of strain energy (SE), is reported. The conversion of a macrocyclic 1,4-diketone to a highly strained arene system takes place over five synthetic steps, featuring iterative dehydrative reactions in the aromatization protocol. Spectroscopic data of the deformed benzenoid macrocycle are in excellent agreement with other homologues that have been reported, indicating that the central p-phenylene ring of 9 is aromatic.
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University , Auburn, Alabama 36849, United States.
authors.forename: Nirmal K
authors.initials: NK
authors.lastname: Mitra
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University , Auburn, Alabama 36849, United States.
authors.forename: Hector H
authors.initials: HH
authors.lastname: Corzo
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University , Auburn, Alabama 36849, United States.
authors.forename: Bradley L
authors.initials: BL
authors.lastname: Merner