Recommanded Product: 3411-48-1. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about Steric and Electronic Effects on the Configurational Stability of Residual Chiral Phosphorus-Centered Three-Bladed Propellers: Tris-aryl Phosphanes. Author is Rizzo, Simona; Benincori, Tiziana; Bonometti, Valentina; Cirilli, Roberto; Mussini, Patrizia R.; Pierini, Marco; Pilati, Tullio; Sannicolo, Francesco.
Triarylphosphines, e.g., tris(2-R,6-X-naphthyl)phosphine (R = Me, Et, X = H, SO3H, OEt), structurally designed to exist as residual enantiomers or diastereoisomers, bearing substituents differing in size and electronic properties on the aryl rings, were synthesized and characterized. Their electronic properties were evaluated from their electrochem. oxidation potential determined by voltammetry. The configurational stability of residual phosphines, evaluated by dynamic HPLC on a chiral stationary phase or/and by dynamic 1H and 31P NMR spectroscopy, is rather modest (barriers of ∼18-20 kcal mol-1), much lower than that shown by the corresponding phosphine oxides (barriers of ∼25-29 kcal mol-1). For the 1st time, the residual antipodes of a triarylphosphine were isolated in enantiopure state and the absolute configuration assigned to them by single-crystal anomalous x-ray diffraction anal. In this case, the racemization barrier could be calculated also by CD signal decay kinetics. A detailed computational study was carried out to clarify the helix reversal mechanism. Calculations indicated that the low configurational stability of tris-aryl phosphines can be attributed to an unexpectedly easy P pyramidal inversion which, depending upon the substituents present on the blades, can occur even on the most stable of the four conformers constituting a single residual stereoisomer.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis