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 journalArticle

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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Lewis Acids
Carbon
Boron
Cyclization
Alkalinity
Computational methods
Titration
Phosphorus
Nuclear magnetic resonance
Association reactions
Experiments
triphenylphosphine
triphenylmethane

Cite this

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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 Br{\o}nsted and Lewis basicities.",
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T1 - Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

AU - Hu, Lei

AU - Mahaut, Damien

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Robiette, Raphaël

AU - Berionni, Guillaume

PY - 2019/9/6

Y1 - 2019/9/6

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AB - 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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