Yields and physicochemical properties:
1-(4-trifluoromethylphenylamino)-1-(4-chlorophenyl)-o,o-diisopropylphosphonate (4a).Yield 64%; m.p.127-128°C; Calculated for C20H24ClNF3PO3 (449.5): 53.40%C, 5.38%H, 3.11%N; found: 53.40%C, 5.39%H, 2.96%N; 1H-NMR: 6.57-7.40 (m, 9H, Ar-H+NH), 4.49-5.18 (m, 3H, 2CH + CH), 2.18 (s, 3H, -CH3), 0.98-1.33 (m, 12H, 4CH3); IR: 3301.7 (?N-H), 1228.4 (?P=0), 1063.0 (?P-O-C), 1100 (?C-F), 121 (?C-F); MS: 449 (M+),284, 172, 145, 123, 111, 82.
1-(4-trifluoromethylphenylamino)-1-(2-fluorophenyl)-o,o-diisopropylphosphonate (4b). Yield 68.0%; m.p.117-118°C; Calculated for C20H24NF4PO3(433): 55.43%C, 5.58%H, 3.23%N; found: 55.40%C, 5.36%H, 3.20%N; 1H-NMR: 6.63-7.49 (m, 9H, Ar-H+NH), 4.42-5.24 (m, 3H, 2CH + CH), 0.86-1.35 (m, 12H, 4CH3); IR: 3302.8 (?N-H), 1231.9 (?P=0), 1065.2 (?P-O-C); MS: 433(M+), 268, 172, 145, 123, 95, 92.
1-(4-trifluoromethylphenyl)-1-(4-fluorophenyl)-O,O-diisopropylphosphonate (4c). Yield 65.0%; m.p. 108-113°C; Calculated for C20H24NF4PO3 (433): 55.43%C, 5.58%H, 3.23%N; found: 55.40%C, 5.45%H, 3.20%N; 1H-NMR: 6.45-7.41 (m, 9H, Ar-H+NH), 4.50-4.71 (m, 3H, 2CH+CH), 2.18 (s, 3H, -CH3), 0.99-1.32 (m, 12H, 4CH3); IR: 3313.4 (?N-H), 1233.6 (?P=0), 1103.8 (?P-O-C).
1-(4-trifluoromethylphenyl)-1-phenyl-O,O-diisopropylphosphonate (4d).Yield 60.3%; m.p.140-142°C; Calculated for C20H25NF3PO3 (414): 57.83%C, 6.07%H, 3.37%N; found: 58.00%C, 5.95%H, 3.30%N; 1H -NMR: 6.59-7.45 (m, 10H, Ar-H+NH), 4.42-4.72 (m, 3H, 2CH+CH), 0. 88-1.33 (m, 12H, 4CH3); IR: 3305.1 (?N-H), 1230.8 (?P=0), 1062.3 (?P-O-C).
1-(4-trifluoromethylphenyl)-1-(4-chlorophenyl)-O,O-diethylphosphonate (4e). Yield 63.13%; m.p. 135-139°C; Calculated for C18H20ClNF3PO3 (421.5): 51.26%C, 4.78%H, 3.32%N; found: 51.28%C, 4.50%H, 3.21%N; 1H-NMR: 6.50-7.41 (m, 9H, Ar-H+NH), 4.05-5.14 (m, 5H, 2CH2+ CH), 1.06-1.30 (m, 6H, 2CH3).
1-(4-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-diethylphosphonate(4f). Yield 44.4%; m.p. 110-111°C; Calculated for C18H20NF4PO3 (405): 53.34%C, 4.97%H, 3.46%N; found: 53.36%C, 4.76%H, 3.34%N; 1H-NMR: 6.59-7.46 (m, 10H, Ar-H+NH), 3.90-5.52 (m, 5H, 2CH2 + CH), 1.03-1.31 (m, 6H, 2CH3); MS: 405(M+), 268, 172, 145, 109, 95, 81.
1-(4-trifluoromethylphenyl)- 1- phenyl-O,O-diethylphosphonate (4g). Yield 24.9%; m.p.141-142°C; Calculated for C18H21NF3PO3 (387): 55.82%C, 5.46%H, 3.62%N; found: 55.76%C, 5.29%H, 3.43%N; 1H-NMR: 6.59-7.45 (m, 9H, Ar-H+NH), 4.42-4.72 (m, 5H, 2CH2+ CH), 1.05-1.31 (m, 6H, 2CH3).
1-(4-trifluoromethylphenyl)-1-(4-chlorophenyl)-O,O-dimethylphosphonate (4h). Yield 30.1%; m.p. 134-135°C; Calculated for C16H16ClNF3PO3 (393.5): 48.81%C, 4.10%H, 4.10%N; found: 48.80%C, 3.98%H, 3.45%N; 1H-NMR: 6.54-7.36 (m, 9H, Ar-H+NH), 3.46-4.61 (m, 7H, 2CH3+ CH).
1-(4-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-dimethylphosphonate (4i). Yield 26.6%; m.p. 110-111°C; Calculated for C16H16NF4PO3 (377): 50.94%C, 4.27%H, 3.71%N; found: 50.80%C, 4.15%H, 3.65%N; 1H-NMR: 6.60-7.47 (m, 9H, Ar-H+NH), 3.46-5.26 (m, 7H, 2CH3+ CH).
1-(4-trifluoromethylphenyl)-1-(4-fluorophenyl)-O,O-dimethylphosphonate (4j). Yield 22.5%; m.p.139-141°C; Calculated for C16H16NF4PO3(377): 50.94%C, 4.27%H, 3.71%N; found 50.94%C, 4.15%H, 3.71%N; 1H NMR: 6.55-7.41(m,9H,Ar-H+NH), 3.46-4.62(m,7H,2CH3+ CH).
1-(4-trifluoromethylphenyl)-1-phenyl-O,O-dimethylphosphonate (4k). Yield 30%; m.p. 97-99°C; Calculated for C16H17NF3PO3 (359): 53.48%C, 4.77%H, 3.90%N; found: 53.94%C, 4.51%H, 3.90%N; 1H-NMR: 6.57-7.42 (m, 10H, Ar-H+NH), 3.40-4.64 (m, 7H, 2CH3+CH).
1-(4-trifluoromethylphenyl)-1-(4-chlorophenyl)-O,O-dipropylphosphonate (4l). Yield 25.0%; m.p. 91-95°C; Calculated for C20H24ClNF3PO3 (449.5): 53.40%C, 5.38%H, 3.11%N; found: 53.35%C, 5.20%H, 2.99%N; 1H-NMR: 6.53-7.39 (m, 9H, Ar-H+NH), 3.62-4.78 (m, 5H, 2CH2+CH), 1.45-1.65 (m, 4H, 2CH2), 0.76-0.93 (m, 6H, 2CH3); MS: 449(M+), 284, 172, 145, 123, 111, 82.
1-(4-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-dipropylphosphonate(4m). Yield 28.0%; m.p. 109-111°C; Calculated for C20H24NF4PO3 (433): 55.43%C, 5.58%H, 3.23%N; found: 55.45%C, 5.40%H, 3.12%N; 1H-NMR: 6.60-7.34 (m, 9H, Ar-H+NH), 3.79-5.23 (m, 5H, 2CH2+CH), 1.38-1.658 (m, 4H, 2CH2), 0.71-0.94 (m, 6H, 2CH3).
1-(4-trifluoromethylphenyl)-1-(4-fluorophenyl)-O,O-dipropylphosphonate (4n). Yield 29.8%; m.p. 95-96°C; Calculated for C 20H24NF4PO3 (433): 55.43%C, 5.58%H, 3.23%N; found: 55.45%C, 5.30%H, 3.15%N; 1H-NMR: 6.53-7.40 (m, 8H, Ar-H), 3.97-4.79 (m, 6H, 2CH2+CH+NH), 1.47-1.65 (m, 4H, 2CH2), 0.75-0.92 (m, 6H, 2CH3); MS: 433(M+), 268, 172, 145, 123, 95,82.
1-(4-trifluoromethylphenyl)-1-(4-chlorophenyl)-O,O-dibutylphosphonate (4o). Yield 69.5%; m.p. 93-95°C; Calculated for C22H28ClNF3PO3 (477.5): 55.29%C, 5.91%H, 2.93%N; found: 55.45%C, 6.15%H, 2.89%N; 1H-NMR: 6.53-7.34 (m, 9H, Ar-H+NH), 4.01-4.77 (m, 5H, 2CH2+CH), 1.23-1.30 (m, 4H, 4CH2), 0.76-0.90 (m, 6H, 2CH3).
1-(4-trifluoromethylphenyl)-1-(4-fluorophenyl)-O,O-dibutylphosphonate (4p). Yield 80.2%; m.p. 92-94°C; Calculated for C22H28NF4PO3 (461): 57.27%C, 6.11%H, 3.04%N; found 57.17%C, 5.95%H, 3.09%N; 1H-NMR: 6.54-7.42 (m, 9H, Ar-H+NH), 3.63-4.76 (m, 5H, 2CH2+CH), 1.19-1.62 (m, 4H, 4CH2), 0.76-0.90 (m, 6H, 2CH3).