Gram-Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9-Tetramethyl[9](2,11)teropyrenophane
Status PubMed-not-MEDLINE Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- EPR spectroscopy, aromaticity, bromination, cyclophanes, structure elucidation,
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
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.
Department of Chemistry Memorial University of Newfoundland St John's NL A1B 3X7 Canada
Department of Chemistry University of Lethbridge 4401 University Drive Lethbridge AB T1K 3M4 Canada
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