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DOI: 10.1055/sos-SD-109-00525

Tobrman, T.Science of Synthesis Knowledge Updates, (20241148.

Unlike 1H-phospholes, phospholide ions are aromatic compounds that are isoelectronic with thiophene. In the solid state, the pure phospholide ions are nearly colorless compounds, but the solutions in tetrahydrofuran are dark red. The reactivity of phospholide ions is affected by their ability to form different aggregates. Zhang and co-workers studied the structure of phospholides in the solid state and found that the crystallization of phospholides 53, 55, and 57 from a mixture of tetrahydrofuran and hexane gave various types of aggregate (Scheme 23).[‌80‌] Depending on the substitution of the heterocyclic ring, phospholide ions crystallize as monomeric complexes such as 54 or as polymeric (e.g., 56) or dimeric aggregates (e.g., 58). Experimental data suggest that the phosphoryl ligand binds preferentially to lithium as an η5-ligand, and the ability of phospholide ions to form different aggregates is affected by temperature, solvent, and the presence of other ligands.

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