6
F. BOUCHAREB ET AL.
[C14H25N2OP] 268. Anal. Calcd for C14H25N2OP: C 62.66, 2H, H–Ar); 6.23 (m, 2H, H–Ar); 6.17 (m, 2H, H–Ar); 4.00
H 9.39, N 10.44. Found: C 62.62, H 9.30, N 10.50%.
(m, 2H, NH). 31P NMR (CDCl3, 100 MHz) d ¼ 16.1 ppm.
13C NMR (CDCl3, 100 MHz): 162.9; 148.3;135.0; 131.5;
130.9; 129.6; 128.6; 110.7; 105.5. MS ESIþ 30 eV m/z: 345.1
[M þ H]þ 100% calcd for [C18H15 F2 N2OP] 344. Anal.
Calcd for C18H15F2N2OP: C 62.79, H 4.39, N 8.14. Found: C
62.75, H 4.35, N 8.24%.
Bis (piperidine) phenylphosphine oxide (8e)
Yield: 91%. Rf¼0.62 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 1591,
1456, 1211. 1H NMR (DMSO, 300 MHz): 7.60 (m, 2H,
H–Ar); 7.30 (m, 3H, H–Ar); 2.95 (t, J ¼ 10.05 Hz, 8H, CH2);
1.65 (m, 8H, CH2) 1.55 (m, 4H, CH2). 31P NMR (DMSO,
100 MHz) d ¼ 16.2 ppm. 13C NMR (DMSO, 100 MHz):
131.0; 130.7; 129.9; 128.1; 127.9; 127.8; 43.9; 22.5; 22.1. MS
ESIþ 30 eV m/z: 293.1 [M þ H]þ 100% calcd for
[C16H25N2OP] 292. Anal. Calcd for C16H25N2OP: C 65.73,
H 8.62, N 9.58. Found: C 65.70, H 8.59, N 9.60%.
Bis (4-chlorophenylamino) phenylphosphine oxide (8j)
Yield: 92%. Rf¼0.68 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3264,
1
1597, 1492, 1275. H NMR (CDCl3, 250 MHz): 7.90 (m, 2H,
H–Ar); 7.50 (m, 3H, H–Ar); 7.02 (m, 4H, H–Ar); 6.40 (m,
4H, H–Ar); 4.00 (m, 2H, NH). 31P NMR (CDCl3, 100 MHz)
d ¼ 16.4 ppm. 13C NMR (CDCl3, 100 MHz): 144.8; 135.0;
131.5; 129.7; 129.6; 128.6; 123.8; 116.5. MS ESIþ 30 eV m/z:
377.1 [M þ H]þ 100% calcd for [C18H15Cl2N2OP] 376. Anal.
Calcd for C18H15Cl2N2OP: C 57.32, H 4.01, N 7.43. Found:
C 57.39, H 4.10, N 7.40%.
Bis (morpholine) phenylphosphine oxide (8f)
Yield: 90%. Rf¼0.68 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 1457,
1200. 1H NMR (CDCl3, 250 MHz): 7.90 (m, 2H, H–Ar);
7.65 (m, 3H, H–Ar); 3.67 (t, J ¼ 8.45 Hz, 8H, CH2–O); 2.90
(t, J ¼ 7.30 Hz, 8H, CH2–N). 31P NMR (CDCl3, 100 MHz)
d ¼ 16.3 ppm. 13C NMR (CDCl3, 100 MHz): 135.0; 131.5;
129.6; 128.6; 72.8; 46.2. MS ESIþ 30 eV m/z: 297.2
[M þ H]þ 100% calcd for [C14H21N2O3P] 296. Anal. Calcs
for C14H21N2O3P: C 56.75, H 7.14, N 9.45. Found: C 56.70,
H 7.10, N 9.50%.
Bis (4-methylphenylamino) phenylphosphine oxide (8k)
Yield: 90%. Rf¼0.66 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3418,
1
1513,1436, 1279. H NMR (CDCl3, 250 MHz): 7.95 (m, 2H,
H–Ar); 7.55 (m, 3H, H–Ar); 6.81 (m, 4H, H–Ar); 6.34 (m,
4H, H–Ar); 4.00 (m, 2H, NH); 2.35 (s, 6H, CH3). 31P NMR
(CDCl3, 100 MHz) d ¼ 16.4 ppm. 13C NMR (CDCl3,
100 MHz): 143.7; 135.0; 131.5; 130.0; 129.6; 128.6; 127.7;
115.0; 20.9. MS ESIþ 30 eV m/z: 337.2 [M þ H]þ 100% calcd
for [C20H21N2OP] 336. Anal. Calcd for C20H21N2OP: C
71.41, H 6.29, N 8.33. Found: C 71.35, H 6.20, N 8.39%.
Bis (cyclohexylamino) phenylphosphine oxide (8g)
Yield: 97%. Rf¼0.62 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3155,
1461, 1250. 1H NMR (CDCl3, 250 MHz): 7.90 (m, 2H,
H–Ar); 7.50 (m, 3H, H–Ar); 3.15 (m, 2H, CH-cyc); 2.40 (m,
2H, NH); 1.90 (m, 4H, CH2-cyc); 1.65 (m, 4H, CH2-cyc);
1.15 (m, 12H, CH2-cyc). 31P NMR (CDCl3, 100 MHz)
d ¼ 16.5 ppm. 13C NMR (CDCl3, 100 MHz): 134.1; 132.4;
129.3; 55.2; 35.1; 25.2; 24.8. MS ESIþ 30 eV m/z: 321.1
[M þ H]þ 100% calcd for [C18H29N2OP] 320. Anal. Calcd
for C18H29N2OP: C 67.47, H 9.12, N 8.74. Found: C 67.50,
H 9.20, N 8.70%.
Bis (4-methoxyphenylamino) phenylphosphine oxide (8l)
Yield: 95%. Rf¼0.67 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3427,
1
1598, 1442, 1258. H NMR (CDCl3, 250 MHz): 7.90 (m, 2H,
H–Ar); 7.50 (m, 3H, H–Ar); 6.52 (m, 4H, H–Ar); 6.35 (m,
4H, H–Ar); 4.00 (m, 2H, NH) 3.73 (s, 6H, CH3). 31P NMR
(CDCl3, 100 MHz) d ¼ 16.4 ppm. 13C NMR (CDCl3,
100 MHz): 152.0; 139.0; 135.0; 131.5; 129.6; 128.6; 116.1;
114.9; 56.0. MS ESIþ 30 eV m/z: 369.2 [M þ H]þ 100% calcd
for [C20H21N2O3P] 368. Anal. Calcd for C20H21N2O3P: C
65.21, H 5.75, N 7.60. Found: C 65.25, H 5.80, N 7.57%.
Bis (phenylamino) phenylphosphine oxide (8h)
Yield: 94%. Rf¼0.67 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3223,
1
1599, 1499, 1293. H NMR (DMSO, 300 MHz): 7.95 (m, 2H,
H–Ar); 7.85 (m, 3H, H–Ar); 7.50 (m, 4H, H–Ar); 7.20 (m,
2H, H–Ar); 6.80 (m, 4H, H–Ar). 31P NMR (DMSO,
100 MHz) d ¼ 17.8 ppm. 13C NMR (DMSO, 100 MHz):
142.6; 132.1; 132.0; 129.2; 128.9; 128.8; 120.7; 118.2; 118.1.
MS ESIþ 30 eV m/z: 309.1 [M þ H]þ 100% calcd for
[C18H17N2OP] 308. Anal. Calcd for C18H17N2OP: C 70.12,
H 5.56, N 9.09. Found: C 70.10, H 5.51, N 9.19%.
Bis (2-methoxyphenylamino) phenylphosphine
oxide (8m)
Yield: 92%. Rf¼0.66 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3414,
1
1599, 1498, 1256. H NMR (CDCl3, 250 MHz): 7.95 (m, 2H,
H–Ar); 7.50 (m, 3H, H–Ar); 6.57 (m, 2H, H–Ar); 6.52 (m,
2H, H–Ar); 6.51 (m, 2H, H–Ar); 6.35 (m, 2H, H–Ar); 4.00
(m, 2H, NH) 3.73 (s, 6H, CH3). 31P NMR (CDCl3,
100 MHz) d ¼ 16.4 ppm. 13C NMR (CDCl3, 100 MHz): 148.6;
135.0; 132.3; 131.5; 129.6; 128.6; 121.6; 119.5; 116.1; 114.9;
Bis (3-fluorophenylamino) phenylphosphine oxide (8i)
Yield: 90%. Rf¼0.67 (CH2Cl2/MeOH). IR (KBr, cmꢀ1): 3415, 56.0. MS ESIþ 30 eV m/z: 369.2 [M þ H]þ 100% calcd for
1
1529, 1494, 1279. H NMR (CDCl3, 250 MHz): 7.90 (m, 2H, [C20H21N2O3P]368. Anal. Calcd for C20H21N2O3P: C 65.21,
H–Ar); 7.50 (m, 3H, H–Ar); 6.99 (m, 2H, H–Ar); 6.33 (m, H 5.75, N 7.60. Found: C 65.25, H 5.80, N 7.57%.