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The Development of Synthetic Routes to 1,1, n , n ‐Tetramethyl[ n ](2,11)teropyrenophanes
Author(s) -
Unikela Kiran Sagar,
Merner Bradley L.,
Ghasemabadi Parisa Ghods,
Warford C. Chad,
Qiu Christopher S.,
Dawe Louise N.,
Zhao Yuming,
Bodwell Graham J.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900707
Subject(s) - chemistry , electrophilic aromatic substitution , electrophile , alkylation , friedel–crafts reaction , electrophilic substitution , pyrene , substitution (logic) , substitution reaction , crystal structure , stereochemistry , crystallography , medicinal chemistry , organic chemistry , catalysis , computer science , programming language
A concise synthetic approach to 1,1, n , n ‐tetramethyl[ n ](2,11)teropyrenophanes has been developed. It involves the construction of triply‐bridged pyrenophanes, during which the three bridges are installed successively using Friedel‐Crafts alkylation, Wurtz coupling and McMurry reactions. At the same time, the innate regiochemical preferences of pyrene toward electrophilic aromatic substitution are relied upon to control the substitution pattern. A cyclodehydrogenation reaction is then employed to generate the teropyrene system directly in a nonplanar conformation. The crystal structure of 1,1,7,7‐tetramethyl[7](2,11)teropyrenophane was determined and the teropyrene system was found to have an end‐to‐end bend angle of 177.9°.