Gram‐Scale Synthesis and Highly Regioselective Bromination of 1, 1, 9, 9‐Tetramethyl[9](2, 11)teropyrenophane. (16th January 2018)

• Record Type: Journal Article
• Authors: Unikela, Kiran Sagar; Roemmele, Tracey L.; Houska, Václav; McGrath, Kaitlin E.; Tobin, David M.; Dawe, Louise N.; Boeré, René T.; Bodwell, Graham J.
• Is Part Of: Angewandte Chemie. Volume 130:Number 6(2018)
• Page Start: 1723
• Page End: 1727
• Publication Date: 2018-01-16
• Subjects: Aromatizität -- Bromierungen -- Cyclophane -- EPR-Spektroskopie -- Strukturaufklärung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201713067
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: An improved synthetic pathway to the nanobelt‐like 1, 1, 9, 9‐tetramethyl[9](2, 11)teropyrenophane 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‐temperature teropyrene‐forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction.