N-Phenyl a-Aminophosphonates
3415
1
3d: R ¼ p-MeO-Ph, colorless liquid. Yield: 35%. H NMR (CDCl3, d ppm):
2
3.75 (s, 3H, CH3), 5.08 (d, 1H, JP-H ¼ 24.38 Hz, CHP), 6.57 (d, 2H,
J ¼ 7.57 Hz, Harom), 6.69 (t, 1H, J ¼ 7.59 Hz, Harom), 6.83 (d, 2H,
J ¼ 6.08 Hz, Harom), 7.05–7.68 (m, 14H, Harom). 31P NMR (CDCl3, d
ppm): 15.89 ppm. Elemental analysis (for C26H24NO4P): calculated (%) C:
70.10, H: 5.43, N: 3.14. Found (%) C: 70.28, H: 5.30, N: 3.34.
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3e: R ¼ Ph, colorless liquid. Yield: 34%. H NMR (CDCl3, d ppm): 5.06
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(d, 1H, JP-H ¼ 24.78 Hz, CHP), 4.83 (br, 1H, NH), 6.56 (d, 2H,
J ¼ 7.66 Hz, Harom), 6.65 (t, 1H, J ¼ 7.66 Hz, Harom), 6.75 (d, 2H,
J ¼ 6.27 Hz, Harom), 6.98–7.48 (m, 15H, Harom). 31P NMR (CDCl3, d
ppm): 15.91 ppm. Elemental analysis (for C25H22NO3P): calculated (%) C:
72.28, H: 5.34, N: 3.37. Found (%) C: 72.44, H: 5.02, N: 3.65.
3f: R ¼ m-Cl-Ph, colorless crystal from diethyl ether–petroleum ether
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(1/5, v/v). Mp: 578C. Yield: 31%. H NMR (CDCl3, d ppm): 5.81 (d, 1H,
2JP-H ¼ 25.60 Hz, CHP), 6.65 (d, 2H, J ¼ 7.77 Hz, Harom), 6.78 (t, 1H,
J ¼ 7.31 Hz, Harom), 6.87 (d, 2H, J ¼ 6.87 Hz, Harom), 7.10–7.41 (m, 13H,
Harom), 7.65–7.67 (m, 1H, Harom). 31P NMR (CDCl3, d ppm): 15.06 ppm.
EI-MS (m/e %): 449 (Mþ, 4), 234 (11), 216 (100), 180 (24), 152 (12), 140
(23), 94 (34), 77 (72), 65 (23), 51 (31), 39 (16). Elemental analysis (for
C25H21ClNO3P): calculated (%) C: 66.75, H: 4.71, N: 3.11. Found (%)
C: 66.89, H: 4.77, N: 3.26.
3g: R ¼ 1-naphthyl, colorless crystal from diethyl ether–petroleum ether (1/
5, v/v). Mp: 828C. Yield: 40%. 1H NMR (CDCl3, d ppm): 5.42 (brs, 1H, NH),
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6.11 (d, 1H, JP-H ¼ 24.51 Hz, CHP), 6.52–8.35 (m, 22H, Harom). 31P NMR
(CDCl3, d ppm): 15.92 ppm. Elemental analysis (for C29H24NO3P): calculated
(%) C: 74.83, H: 5.20, N: 3.01. Found (%) C: 74.47, H: 5.51, N: 3.37.
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3h: R ¼ n-Pr, colorless liquid. Yield: 47%. H NMR (CDCl3, d ppm): 0.91
(t, 3H, J ¼ 7.37 Hz, CH3), 1.22–1.43 (m, 2H, CH2), 1.65–1.81 (m, 2H,
CH2), 3.92 (m, 1H, CHP), 6.51 (d, 2H, J ¼ 7.50 Hz, Harom), 6.69 (t, 1H,
J ¼ 7.48 Hz, Harom), 6.90 (d, 2H, J ¼ 6.77 Hz, Harom), 7.06–7.23 (m, 10H,
H
arom). 31P NMR (CDCl3, d ppm): 19.20 ppm. Elemental analysis (for
C22H24NO3P): calculated (%) C: 69.28, H: 6.34, N: 3.67. Found (%) C:
69.02, H: 5.98, N: 3.31.
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3i: R ¼ i-Pr, colorless liquid. Yield: 46%. H NMR (CDCl3, d ppm): 0.95–
1.27 (m, 6H, 2CH3), 2.28–2.49 [m, 1H, CH(CH3)2], 3.92 (br, 1H, NH),
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3
3.98 (dd, JP-H ¼ 18.04 Hz, JH-H ¼ 5.43 Hz, CHP), 6.55 (d, 2H,
J ¼ 7.54 Hz, Harom), 6.66 (t, 1H, J ¼ 7.58 Hz, Harom), 6.86 (d, 2H,
J ¼ 6.82 Hz, Harom), 7.04–7.21 (m, 10H, Harom). 31P NMR (CDCl3, d
ppm): 19.29 ppm. Elemental analysis (for C22H24NO3P): calculated (%)
C: 69.28; H: 6.34; N: 3.67. Found (%) C: 69.59; H: 6.43; N: 3.78.