Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 17, Pages 11268-11274Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01570
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Funding
- University of Namur
- Namur Institute of Structured Matter (NISM)
- Fond National de la Recherche Scientifique FNRS (MIS) [F.4513.18]
- FNRS [2.5020.11]
- Walloon Region
- China Scholarship Council (CSC) [201606670003]
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Two practical and high-yielding syntheses of 9-phosphatriptycene are reported. In both approaches, the key step is based on the cyclization of a (tris)lithio-triphenylmethane or a (tris)lithio-triphenylphosphine intermediate on a phosphorus or a carbon electrophile, respectively. The association of 9-phosphatriptycene with representative boron- and carbon-centered Lewis acids was investigated by IR, NMR, and UV-vis titration experiments and by computational methods, shedding light on its steric hindrance, sigma-donating ability, and Brensted and Lewis basicities.
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