Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

The Journal of Organic Chemistry
Lei HuGuillaume Berionni

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

Nov 25, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Siva Sankar Murthy BandaruAnant R Kapdi
Mar 18, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Lei HuGuillaume Berionni

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