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

Lei Hu, Damien Mahaut, Nikolay Tumanov, Johan Wouters, Raphaël Robiette, Guillaume Berionni

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)11268-11274
Number of pages7
JournalJournal of Organic Chemistry
Volume84
Issue number17
DOIs
Publication statusPublished - 6 Sep 2019

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