title: Phthalocrowns: isoindoline-crown ether macrocycles.
abstract: The reaction of diiminoisoindoline with amine-terminated polyethers results in the formation of phthalocrown macrocycles. For n = 1 (where n is the number of ether units), a 2 + 2 condensation takes place, but for n = 2 and 3, a 1 + 1 macrocycle formation occurs. The n = 2 phthalocrown is particularly stable due to a strong intramolecular hydrogen bond, but the n = 3 ring hydrolyzes to form a 3-imino-1-oxoisoindoline derivatized crown ether species. For the n = 1 phthalocrown, we observed dynamic behavior in the (1)H NMR spectrum, and using VTNMR were able to measure a ΔG(‡) = 44.6 kJ/mol for proton exchange.
authors.affiliation: Department of Chemistry, University of Akron, Akron, Ohio 44325-3601, USA.
authors.forename: Ingrid-Suzy
authors.initials: IS
authors.lastname: Tamgho
authors.forename: James T
authors.initials: JT
authors.lastname: Engle
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Ziegler