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(46.65), 74 (38.74), 63 (92.49), 44 (84.65). Anal. Calc. for
C10H10Cl2NaO6P: C, 34.21, H, 2.87. Found: C, 34.46,
H, 3.13%.
–C6H3); MS m/z (ion, rel. int.): 392 (M+ 0.05), 234
(41.23), 220 (11.01) 199 (83.16), 175 (70.88), 162 (100),
145 (33.53), 139 (88.36), 133 (33.46), 111 (72.03), 109
(35.91), 98 (32.18), 94 (0.93), 93 (7.61), 75 (54.97), 74
(40.70), 63 (63.03), 44 (31.06). Anal. Calc. for
C13H16Cl2NaO6P: C, 39.72, H, 4.10, Found: C, 39.28,
H, 3.86%.
4.5.2. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)-
ethylphosphonate monosodium (6b)
Compound 6b was isolated as a white solid (84%
yield): m.p. = 46–47 °C; IR (neat cmꢁ1): 3008 (mPh–H),
2947 (mC–H), 1754 (mC@O), 1178 (mP@O), 1070 (mC–
4.5.5. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)-
pentylphosphonate monosodium (6e)
1
O–C), 1045 (mP–O–C), 795 (mP–C); H NMR (d/ppm):
1.26 (q, JHH = 8.00 Hz, 3H, –CH3), 3.35 (d,
3
Compound 6e was isolated as a light yellow solid (52%
yield): m.p. = 163–165 °C; IR (neat cmꢁ1): 3012 (mPh–
H), 2947 (mC–H), 1743 (mC@O), 1186 (mP@O), 1079
3JHP = 10.00 Hz, 3H, –OCH3), 4.84 (s, 2H, –OCH2-
2
CO–), 4.89 (d, JHP = 10.20 Hz, 1H, –OCHP), 7.02–
7.54 (m, 3H, –C6H3); MS m/z (ion, rel. int.): 364 (M+
0.2), 234 (2.59), 220 (14.03), 199 (4.28), 175 (16.09),
162 (100), 145 (10.90), 133 (14.30), 123 (2.91), 111
(14.80), 109 (25.85), 98 (28.36), 94 (1.09), 93 (18.56),
75 (13.45), 74 (10.55), 63 (40.42), 44 (26.29); LC-MS
m/z (ion, rel. int.): 341(M+ ꢁ23, 11.44), 219 (73.8),
161(100), 139(67.24), 127(22.49), 387 (M+ +23, 22.87),
364 (M+ 9.35), 175 (32.78). Anal. Calc. for
C11H12Cl2NaO6P: C, 36.19, H, 3.31. Found: C, 35.98,
H, 3.26%.
1
(mC–O–C), 1054 (mP–O–C), 748 (mP–C); H NMR (d/
ppm): 0.83 (t, JHH = 6.63 Hz, 3H, –CH2CH2CH2CH3),
1.14–1.28 (m, 4H, –CH2CH2CH2CH3), 1.58–1.74 (m,
3
3
2H, –CH2CH2CH2CH3), 3.35 (d, JHP = 9.00 Hz, 3H,
2
–OCH3), 4.83(d, JHH = 16.53 Hz, 1Ha, –OCH2CO–),
2
4.98(d, JHH = 16.53 Hz, 1Hb, –OCH2CO–); 5.04 (d,
2JHP = 9.80 Hz, 1H, –OCHP), 7.02–7.56 (m, 3H,
–C6H3); MS m/z (ion, rel. int.): 406 (M+ 0.03), 234
(7.83), 220 (5.33) 199 (11.98), 175 (21.39), 162 (89.87),
145 (8.35), 142 (100), 139 (77.85), 133 (13.17), 111
(34.68), 109 (6.67), 98 (31.62), 94 (0.29), 93 (0.88), 75
(30.77), 74 (20.51), 63 (47.52), 44 (9.53). Anal. Calc. for
C14H18Cl2NaO6P: C, 41.30, H, 4.46. Found: C, 41.04,
H, 4.18%.
4.5.3. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)-
propylphosphonate monosodium (6c)
Compound 6c was isolated as a light yellow solid
(64% yield): m.p. = 81–83 °C; IR (neat cmꢁ1):
3015 (mPh–H), 2948 (mC–H), 1738 (mC@O), 1198
(mP@O), 1090 (mC–O–C), 1050 (mP–O–C), 742 (mP–C);
4.5.6. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)2,2,2-
trichloroethylphosphonate monosodium (6f)
3
1H NMR (d/ppm): 0.84 (t, JHH = 7.41 Hz, 3H,
–CH2CH3), 1.55–1.86 (m, 2H, –CH2CH3), 3.35 (d,
2
Compound 6f was isolated as a white solid (65%
yield): m.p. = 121–123 °C; IR (neat cmꢁ1): 3086 (mPh–
H), 2947 (mC–H), 1742 (mC@O), 1251 (mP@O), 1079
(mC–O–C), 1054 (mP–O–C), 749 (mP–C); 1H NMR
3JHP = 9.72 Hz, 3H, –OCH3), 4.79 (d, JHH = 9.87 Hz,
2
1Ha, –OCH2CO–), 4.84 (d, JHH = 11.40 Hz, 1Hb,
2
–OCH2CO–), 5.01 (d, JHP = 16.59 Hz, 1H, –OCHP),
3
7.07–7.59 (m, 3H, –C6H3); MS m/z (ion, rel. int.): 378
(M+ 0.1), 234 (14.35), 220 (15.98), 199 (43.15), 185
(4.30), 175 (70.19), 162 (77.72), 145 (43.19), 133
(41.88), 111 (61.57), 109 (85.39), 105 (52.92), 98
(33.16), 94 (3.78), 93 (100), 77 (63.71), 75 (40.19), 74
(37.69), 63 (93.51), 44 (52.01). Anal. Calc. for
C12H14Cl2NaO6P: C, 38.02, H, 3.72, Found: C, 37.87,
H, 3.46%.
(d/ppm): 3.30 (d, JHP = 9.71 Hz, 3H, –OCH3), 3.98 (d,
2JHP = 7.76 Hz 1H, –OCHP), 4.85 (s, 2H, –OCH2CO–),
6.99–7.49 (m, 3H, –C6H3). Anal. Calc. for
C11H9Cl5NaO6P: C, 28.21, H, 1.94. Found: C, 27.83,
H, 2.08%.
4.5.7. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)-
methylphosphonate monopotassium (6g)
4.5.4. O-Methyl-1-(2,4-dichlorophenoxyacetoxy)-
butylphosphonate monosodium (6d)
Compound 6g was isolated as a white solid (61%
yield): m.p. = 162–164 °C; IR (neat cmꢁ1): 3062 (mPh–
H), 2958 (mC–H), 1740 (mC@O), 1234 (mP@O), 1072
Compound 6d was isolated as a light yellow solid
(51% yield): m.p. = 110–112 °C; IR (neat cmꢁ1): 3009
(mPh–H), 2950 (mC–H), 1740 (mC@O), 1188 (mP@O),
1
(mC–O–C), 1056 (mP–O–C), 736 (mP–C); H NMR (d/
ppm): 3.35 (d,3JHP = 7.28 Hz, 3H, -OCH3), 4.02 (d,
2JHP = 8.10 Hz, 2H, –OCH2P), 4.91 (s, 2H, –OCH2-
CO–), 7.08–7.69 (m, 3H, –C6H3); MS m/z (ion, rel.
int.): 366 (M+ 0.39), 234 (0.76), 220 (0.37), 199 (0.68),
175 (1.62), 162 (2.93), 133 (1.47), 127 (1.75), 109
(6.20), 94 (2.36), 93 (2.98), 63 (21.64), 45 (100). Anal.
Calc. for C10H10Cl2KO6P: C, 32.71, H, 2.75. Found:
C, 32.42, H, 2.89%.
1
1086 (mC–O–C), 1048 (mP–O–C), 756 (mP–C); H NMR
3
(d/ppm): 0.83 (t, JHH = 7.39 Hz, 3H, –CH2CH2CH3),
1.15–1.39 (m, 2H, –CH2CH2CH3), 1.58–1.74 (m, 2H,
3
–CH2CH2CH3), 3.35 (d, JHP = 9.72 Hz, 3H, –OCH3),
2
4.83 (d, JHH = 16.57 Hz, 1Ha, –OCH2CO–), 4.96(d,
2JHH = 16.56 Hz,
1Hb,
–OCH2CO-);
5.02
(d,
2JHP = 9.90 Hz, 1H, –OCHP), 7.07–7.59 (m, 3H,