Gram-Scale Synthesis of the 1,1,n,n-Tetramethyl[n](2,11)teropyrenophanes |
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| Authors: | Dr Kiran Sagar Unikela Dr Parisa Ghods Ghasemabadi Dr Václav Houska Dr Louise N Dawe Dr Yuming Zhao Dr Graham J Bodwell |
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| Institution: | 1. Department of Chemistry, Memorial University of Newfoundland, 283 Prince Philip Drive, St. John's, NL, A1B 3X7 Canada;2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic;3. Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Avenue West, Waterloo, ON, N2L 3C5 Canada |
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| Abstract: | A gram-scale synthesis of a series of 1,1,n,n-tetramethyln](2,11)teropyrenophanes (n=7–9) has been accomplished as well as the first synthesis of the next higher homologue 1,1,10,10-tetramethyl10](2,11)teropyrenophane. The scale-up of the original small-scale synthesis required the development of several heavily modified synthetic methods, including a chlorination/Friedel–Crafts alkylation protocol and an iodination/Wurtz coupling protocol, which were performed on 25–30 g and 30–60 g scales, respectively. Two separate sets of conditions for the key teropyrene-forming cyclodehydrogenation reaction at the end of the synthetic pathway were developed, an acid-promoted one for the two less strained congeners and an acid-free method for the two more strained homologues. |
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| Keywords: | cyclodehydrogenation cyclophanes nonplanar aromatic compounds pyrene teropyrene |
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