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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of triarylphosphines and triarylphosphine oxides through the use of organolithium compounds》. Authors are Mikhailov, B. M.; Kucherova, N. F..The article about the compound:Tri(naphthalen-1-yl)phosphinecas:3411-48-1,SMILESS:C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2).SDS of cas: 3411-48-1. Through the article, more information about this compound (cas:3411-48-1) is conveyed.
All operations with RLi were run in a N atm. To a solution of PhLi (from 5 g. PhBr, 0.44 g. Li, and 30 ml. absolute Et2O) was added with cooling over 15-20 min. 1.3 g. PCl3 in 20 ml. Et2O, the mixture was decompose with H2O after subsidence of reaction, and the organic layer washed with 10% NaOH to give 1.9 g. (61.3%) Ph3P, m. 77-8° (from EtOH). Similarly ArLi from 4 g. 1-C10H7Br, 0.27 g. Li, and 55 ml. Et2O, treated with 0.9 g. PCl3 in 50 ml. Et2O, water added, the mixture made alk. with NaOH, and the organic layer evaporated, gave 26.9% (1-C10H7)3P, m. 276-8°; crystallized from CHCl3 it forms a CHCl3 adduct, m. 260-2°, losing the solvent at 110°; the pure product m. 278-80°. 9-Bromophenanthrene, (5 g.) added to a BuLi solution from 3 g. BuCl, 0.5 g. Li, and 30 ml. Et2O, precipitated the Li derivative; the solution decanted and the washed precipitate suspended in fresh Et2O and treated with 0.9 g. PCl3 in Et2O, gave a red color which vanished as the addition continued; the usual treatment gave 72% tri-9-phenanthrylphosphine, m. 374-6° (from MePh). Similarly, 9-bromoanthracene gave 20% tri-9-anthrylphosphine, m. 270-3° (from C6H6), and some 18% anthracene. To 0.017 mole PhLi in 32 ml. Et2O was added 5 g. 9,10-dibromoanthracene and, after 20 min., 0.67 g. PCl3 in 15 ml. Et2O, yielding a red solution and precipitate; after 10 min. the usual treatment gave 3.1 g. crude product, which, extracted with hot MePh, gave 1.2 g. tris(9-bromo-10-anthryl)phosphine, orange-yellow, m. 206-8°. To BuLi from 1.1 g. BuCl, 0.2 g. Li, and 20 ml. Et2O was added 2 g. 7-bromobenz[a]anthracene, then 0.35 g. PCl3 in Et2O; the usual treatment gave 53% tris(1,2-benz[a]anthracen-7-yl)phosphine, m. 192-4° (after treatment with hot C6H6). PhLi solution with POCl3 gave 65% Ph3PO, m. 155-7° (from Et2O); 1-C10H7Li gave after 0.5 hr., 38.5% tri-1-naphthylphosphine oxide, m. 335-6.5° (from much CHCl3); 9-phenanthryllithium gave after 10 min. 49% tri-9-phenanthrylphosphine oxide, m. 354-6° (from MePh); while 10-bromo-1,2-benzanthracene yielded tris(benz[a]-anthracen-7-yl)phosphine oxide, m. 191-3° (from C6H6-Et2O). The reaction with POCl3 is vigorous and is best run with ice cooling.
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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