Citation:
Unikela KS, Roemmele TL, Houska V, McGrath KE, Tobin DM, Dawe LN, Boeré RT, Bodwell GJ. Gram-Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9-Tetramethyl[9](2,11)teropyrenophane. Angewandte Chemie, International Edition [Internet]. 2018;57(6):1707-1711.
Abstract:
An improved synthetic pathway to the nanobelt-like 1,1,9,9-tetramethyl[9](2,11)teropyrenophane(I) has been developed, and enables the synthesis of gram quantities of material. Key innovations are the development of a sequential chlorination/Friedel-Crafts alkylation reaction, a sequential iodination/Wurtz coupling reaction, and a room-temp. teropyrene-forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction. Safety: care required for exothermic Grignard.