Synthesis of oligomeric chains with 9,10‐dihydroanthracene units by carbanion alkylation

Deprotonation of 9,10‐dihydroanthracene (2) affords the monoanion 6 which is subjected to alkylation reactions with mono and bifunctional electrophiles. Crucial intermediates in syntheses using 6 are 9‐(3‐bromopropyl)‐9,10‐dihydroanthracene (7) and 1,3‐bis(9,10‐dihydro‐9‐anthryl)propane (9) since they provide access to linear oligomers in which 9,10‐dihydroanthracene units are linked by trimethylene groups. The alkylation processes of these species can be extended to the structurally related polymer 4. The regio‐ and stereoselectivity of the alkylation reactions are investigated by 1H‐ and 13C‐NMR spectroscopy.