Microwave Synthesis of Trichlorfon and Derivatives
31
2257
◦
◦
1
(
3a). m.p. 75–76 C (lit. 76–78 C). P NMR (CDCl3) δ: 18.83. H NMR
3
3
(
CDCl3) δ: 3.88 (d, JP−H = 6.5 Hz, 3H, POCH3), 3.93 (d, JP−H = 6.5
2
Hz, 3H, POCH3), 5.45 (d, JP−H = 11.75, 1H, CHOH), 5.48 (s, 1H, OH).
1
2
2
3
1
2
C { H}NMR (CDCl3) δ 54.22 (d, JP−C = 27.5 Hz, POCH3), 54.80 (d,
1
JP−C = 27.5 Hz, POCH), 79.98 (d, JP−C = 665 Hz, CHOH), 97.75 (d,
−1
JP−C = 6.8 Hz, CCl). IR (KBr) cm : 3350, 3042, 2980, 2940, 1270, 1200
(
P O).
◦
◦
31
1
(
3b). m.p. 54–55 C (lit. 55–56 C). P NMR (CDCl3) δ: 16.37. H
4
NMR (CDCl3) δ: 1.38 (t, JP−H = 7.0, 6H, POCH2CH3), 4.28 (m,
4
H, POCH2CH3), 4.49 (d, J = 11.75, 1H, CHOH), 5.86 (s, 1H, OH).
1
3
3
3
C{1H}NMR (CDCl3) δ16.36 (d, JP−C = 5 Hz, POCH2CH3), 16.46 (d,
2
JP−C = 5 Hz, POCH2CH), 64.28 (d, JP−C = 27.5 Hz, POCH2CH3), 64.33
2
1
(
9
2
d, JP−C = 27.5 Hz, POCH2CH3), 78.99 (d, C(P)OH, JP−C = 657.5 Hz),
2
−1
8.04 (d, 1C, JP−C = 40 Hz, CCl). IR (KBr) cm : 3355, 3100, 3020,
980, 1280, 1230, 1205 (P O).
◦
◦
(
3c). m.p. 108–109 C (lit. 105–106 C). 31P NMR (CDCl3) δ: 14.49.
1
3
H NMR (CDCl3) δ: 1.39 (d, JH−H = 7.0, 8.1, 6H, CH(CH3)2, 1.39 (d,
3
JH−H = 7.0, 6H, CH(CH3)2, 4.39 (d, 1H, J = 11.75, CHOH), 4.86 (m,
13
1
H, CH(CH3)2), 5.49 (sb, 1H, OH). C{1H}NMR (CDCl3) δ: 23.74 (d,
3
3
JP−C = 25 Hz, CH(CH3)2), 24.34 (d, JP−C = 25 Hz, CH(CH3)), 24.44 (d,
3
2
JP−C = 25 Hz, CH(CH3)2),73.17 (d, JP−C = 30 Hz, CH(CH3)2), 73.83
2
1
(
9
2
d, JP−C = 32.5 Hz, CH(CH3)2), 80.20 (d, JP−C = 655 Hz, C(P)OH),
2
−1
8.27 (d, JP−C = 37.5 Hz, CCl3). IR (KBr film) cm : 3350, 3065, 3010,
950, 1290, 1270, 1200 (P O).
REFERENCES
[
[
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[
[
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[
[
[
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(
(
b) A. R. Hajipour, S. E. Mallakpour, and Gh. Imanzadeh, J. Chem. Res. (S), 228
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[
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[
[
[
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