Planar Polycyclic Oxaphosphoranes Incorporating a Benzophosphole Unit

Abstract

A facile method to synthesize quaternized benzophospholes on gram scale was reported, and the products were isolated by simple filtration. During this research, a series of σ-oxaphosphoranes incorporating polycyclic aromatic hydrocarbons (PAHs) were obtained. The grafting of α-phenolate groups on the phosphorus center enhances the coplanarity of the system.

Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes

“…Their treatment with oxalyl chloride gives electrophilic λ 5 σ 5 ‐chlorophosphonium intermediates, which then transform into the heterocycle at moderately elevated temperature (70 °C, route C, Scheme 7). [55] …”

Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides

“… 25 Their ortho analogues with phosphorus at a lower oxidation state are typically used for the construction of the benzophosphole skeleton. 26 The access to those derivatives was achieved via a reaction of o- lithiotolane with chlorophosphine ( Scheme 1 A). 26e , 27 A different route to these derivatives was completed through Sonogashira coupling.…”

“…Those compounds have found several applications in the construction of star-shaped fluorescent molecules, microporous organic polymers (MOPs), nanostructured carbon materials, and triazole precursors . Their ortho analogues with phosphorus at a lower oxidation state are typically used for the construction of the benzophosphole skeleton . The access to those derivatives was achieved via a reaction of o- lithiotolane with chlorophosphine (Scheme A). , A different route to these derivatives was completed through Sonogashira coupling .…”

Diversified Aggregation States of Phospholyl Lithiums

“…As analogues of cyclopentadienyl anions which could form sandwich complexes, inverted-sandwich complexes, and one-dimensional coordination polymers, phospholyl anions have attracted much attention because they can stabilize many metal complexes by both their delocalized 6π aromatic systems and the lone pairs on the phosphorus. − Phospholyl lithiums are the fundamental precursors for the synthesis of other metal complexes supported by phospholyl anions. The reactivity of phospholyl lithiums toward metal halides is significantly dependent on the aggregation state.…”