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Updated: Sep 6, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
π-Delocalization in phosphaphthalimide and its ambident reactivity (O/P) toward main-group electrophiles
Qi Shen1, Jiashi Xu1, Xiaodan Chen1
1Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China. chxdlzhsh@jnu.edu.cn.
Abstract:
The report on phosphaphthalimide (1), the phosphorus analogue of the phthalimide anion, dates back to forty years ago. However, the presence of π-delocalization between two-coordinated phosphorus centre and neighbouring carbonyl groups in 1 has been underestimated. Herein, sodium salts of 1 were obtained through a convenient procedure on a relatively large scale with a modified procedure. Reactivity studies demonstrated that 1 is indeed a good electrophile and the essential role of π-delocalization in 1 controlling its ambident properties. NBO analysis revealed the p-π conjugation and p-σ* hyperconjugation in 1 affecting its bond lengths in opposite ways.
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