Synthesis and Structure of Functionalized Zigzag Hydrocarbon Belts

Described in this paper are the synthesis and structure of novel and edge-functionalized zigzag hydrocarbon belts. A stepwise fjord-stitching strategy featuring repetitive intramolecular acylation reactions of a resorcin[4]arene derivative as the key steps afforded a biscarbonyl-functionalized octahydrobelt[8]arene product. Facile ketone reduction with NaBH(4)and nucleophilic addition withn-butyllithium produced secondary and tertiary alcohol-containing molecular belts, respectively. Selective oxidation reactions of biscarbonyl-bearing octahydrobelt[8]arene withm-CPBA and (PhSeO)(2)O furnished the corresponding lactone- and 1,4-quinone-embedded molecular belts. Depending on the functional groups on the edges, the acquired belt molecules adopt different shapes such as square prism, truncated cone, and elliptical cylinder.