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, Hydrogen peroxide (30 % solution, 1.7 mL) was slowly added to a solution of di- phenyl-[4-trimethylsilylethynyl)phenyl]phosphane (2 g, 5.58 mmol) in a mixture of dichloromethane (50 mL) and methanol (50 mL) The resulting mixture was stirred at room temperature for 2 h and was then quenched with aqueous Na 2 SO 3 solution and extracted with dichloromethane, The combined organic phases were dried (MgSO 4 ), filtered, and concentrated under reduced pressure to give a white solid, p.96
, 25 ppm (s, 9 H; CH 3 ), H NMR (300 MHz C NMR (75 MHz, CHCl 3 ): 132.7 (C-P) P NMR (121 MHz, pp.139-147
, g, 5.34 mmol) in a mixture of dichloromethane (40 mL) and methanol (60 mL) The resulting mixture was stirred at room temperature for 2 h, quenched with water, and then extracted with dichloromethane. The combined organic layers were dried (MgSO 4 ), filtered, and concentrated under reduced pressure to give a white solid (1.4 g, 85 %). M.p. 144 8C; 1 H NMR (300 MHz, CHCl 3 ): d = 7 (m, 10 H; H ar ), 7 (m, 4 H; H ar ), 3.20 ppm (s, 1 H; H C= CH ); 13 C NMR (75 MHz, CHCl 3 ): d = 133 mmol) were added to a solution, Diphenyl-(4-ethynylphenyl)phosphane oxide (2 d): Potassium carbonate (256 mg 82.6, 79.9 ppm (2 ” C, C=C); 31 P NMR (121 MHz, CDCl 3 ): d = 28.7 ppm; MS (CI, NH 3 ): C 20 H 15 H NMR (300 MHz, CHCl 3 ): d = 8, pp.69-76
, KGaA, Weinheim www.chemeurj.org 9063 FULL PAPER Fluorescent Phosphane Oxides (m, 2 H; H 1ar ) H; H 6ar ), 3.05 ppm (s, 6 H; CH 3 ), 3ar , H 5ar ), 6.76 (d, J = 9.2 Hz C NMR (75 MHz, CHCl 3 ): d = 150.6 (C) ” C), pp.9056-906557, 2006.
, CuI (1.91 mg, 0.01 mmol)PPh 3 ) 4 (12 mg, 0.01 mmol) were added to a solution of 10 (145 mg, 0.33 mmol) and the phosphane oxide 2 d (100 mg, 0.33 mmol) in a mixture of toluene (15 mL) and triethylamine (4 mL) The resulting mixture was stirred at room temperature for 24 h at 50 8C, and was then allowed to cool to room temperature and concentrated under vacuum. The residue was purified by silica gel chromatography (dichloromethane/acetone 95:5) to give an orange solid (70 mg, pp.73-81
, 06 ppm (s, 6 H; CH 3 ) CHCl 3 ): d = 150, C NMR (75 MHz 132.5 (2 ” CH ar, pp.131-137
, Compound 2 b was obtained by the same experimental procedure as used to prepare 3, starting from a solution of [4- (4-iodophenylethynyl)phenyl]-dimethylamine (6, 527 mg, 1.51 mmol) and the phosphane oxide 2 d (100 mg, 0.33 mmol) in a mixture of toluene (18 mL) and triethylamine (4 mL) with CuI (14 mg, 0.07 mmol) and, to afford a yellow solid (316 mg, 67 %). M.p
, 66 (d, J = 9 Hz, 2 H; H ar ), 2.99 ppm (s, 6 H; CH 3 ); 13 C NMR (100 MHz, CHCl 3 ): d = 150, 8C; 1 H NMR (300 MHz ” C ar ) ” CH ar ), 131.3 (2 ” CH ar 40.3 ppm (2 ” CH 3 ); 31 P NMR (121 MHz, pp.70-77
, Compound 1 b was prepared by the same experimental procedure as used to prepare 3, starting from a solution of [4-(4-iodophe- nylethynyl)phenyl]dimethylamine (6, 600 mg, 1.75 mmol) and tris-(4- ethynylphenyl)phosphane oxide (1 d, 121 mg, 0.35 mmol) in a mixture of toluene (20 mL) and triethylamine (4 mL) with CuI (16 mg, 0.07 mmol)PPh 3 ) 4 (44 mg, 0.035 mmol), to afford a yellow solid (261 mgs, 18 H; CH 3 ); 13 C NMR (100 MHz, CHCl 3 ): d = 150, ” CÀP), pp.246-248
, Compound 1 c was obtained by the same experimental procedure as used to prepare 3, starting from a solution of (4-iodophenyl)-dimethylamine (9, 500 mg, 2 mmol) and tris-(4-ethynylphenyl)phosphane oxide (1 d, 177 mg, 0.5 mmol) in a mixture of toluene (26 mL) and triethylamine (7 mL) with CuI (19 mg, 0.1 mmol) and mmol), to afford a yellow solid (110 mg, p.40
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, Penhoat are respectively grateful to the Ministère de l'Education et de la Recherche and C.N.RS. for grants, 2004.