title: Oligospiroketals as novel molecular rods.
abstract: A modular approach for the synthesis of molecular rods based on oligospiroketals has been developed. The strategy relies on different terminal and intermediate segments, which are joined by ketal formation between ketones and diols. For this purpose it was necessary to develop a new ketalization method to circumvent some problems related with the established methods. The terminal segments are either derived from 4-piperidinone or from 4-oxocyclohexane carboxylic acid whereas the intermediate segments rest on pentaerythritol and cyclohexane-1,4-dione. A series of trispiro (14-18), hexaspiro (19) and nonaspiro (20) compounds have been prepared and characterized. From these we realized that it is imperative to use solubility enhancing groups if more than seven rings are joined.
authors.affiliation: Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Strasse 2, 12489 Berlin, Germany. pablo.wessig@chemie.hu-berlin.de
authors.forename: Pablo
authors.initials: P
authors.lastname: Wessig
authors.forename: Kristian
authors.initials: K
authors.lastname: Möllnitz
authors.forename: Christiane
authors.initials: C
authors.lastname: Eiserbeck
mesh_terms: D008968:Molecular Conformation; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D013141:Spiro Compounds