title: Heteroaromatic belts through fold-in synthesis: mechanistic insights into a macrocycle-templated Friedel-Crafts alkylation.
abstract: Direct alkylation of 9,9',9''-triethyl[2.2.2](2,7)carbazolophane with dimethoxymethane or paraformaldehyde affords a belt-like heteroaromatic structure, which forms as a kinetic product in acid-catalyzed condensations. In a competing, thermodynamically favored process, polymeric structures are formed by a largely regioselective condensation of stereochemically rigid "semi-belts". The relationship between these reactivity routes is rationalized in terms of strain release and differential reversibility of consecutive condensation steps.
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski ul. F. Joliot-Curie 14, 50-383 Wrocław (Poland) http://www.mstepien.edu.pl.
authors.forename: Mateusz
authors.initials: M
authors.lastname: Kondratowicz
authors.forename: Damian
authors.initials: D
authors.lastname: Myśliwiec
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Lis
authors.forename: Marcin
authors.initials: M
authors.lastname: Stępień
keywords: cyclophanes; electrophilic substitution; fused ring systems; nitrogen heterocycles; polymers