Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure–Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids
(2019) The Journal of Organic Chemistry — Vol. 84, n° 17, p. 11268-11274 (2019)
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- Authors
Tumanov, Nikolay 
Berionni, Guillaume
- Abstract
- 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, σ-donating ability, and Brønsted and Lewis basicities.
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Citations
Hu, L., Mahaut, D., Tumanov, N., Wouters, J., Robiette, R., & Berionni, G. (2019). Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure–Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids. The Journal of Organic Chemistry, 84(17), 11268-11274. https://doi.org/10.1021/acs.joc.9b01570 (Original work published 2019)