1005496-91-2Relevant academic research and scientific papers
Insertion of CO2, ketones, and aldehydes into the C-Li bond of 1,3,5-triaza-7-phosphaadamantan-6-yllithium
Wong, Gene W.,Lee, Wei-Chih,Frost, Brian J.
, p. 612 - 620 (2008/10/09)
The synthesis and structures of a series of new water-soluble phosphine ligands based on 1,3,5-triaza-7-phosphaadamantane (PTA) are described. Insertion of aldehydes or ketones into the C-Li bond of 1,3,5-triaza-7-phosphaadamantan- 6-yllithium (PTA-Li) resulted in the formation of a series of slightly water-soluble β-phosphino alcohols (PTA-CRR′OH, R = C 6H5, C6H4OCH3, ferrocenyl; R′ = H, C6H5, C6H 4OCH3) derived from the heterocyclic phosphine PTA. Insertion of CO2 yielded the highly water-soluble carboxylate PTA-CO2Li, S25° ≈ 800 g/L. The compounds have been fully characterized in the solid state by X-ray crystallography and in solution by multinuclear NMR spectroscopy. The addition of PTA-Li to symmetric ketones results in a racemic mixture of PTA-CR2OH ligands with a single resonance in the 31P{1H} NMR spectrum between -95 and -97 ppm. The addition of PTA-Li to aldehydes results in a mixture of diasteromeric compounds, PTA-CHROH, with two 31P{1H} NMR resonances between -100 and -106 ppm. Three (η6-arene)RuCl 2(PTA-CRR′OH) complexes of these ligands were synthesized and characterized, with the ligands binding in a κ1 coordination mode. All the ligands and ruthenium complexes are slightly soluble in water with S25° = 3.9-11.1 g/L for the PTA-CRR′OH ligands and S 25° = 3.3-14.1 g/L for the (η6-arene)RuCl 2(PTA-CRR′OH) complexes.
