10
AITKEN ET AL.
[(Acetyl)(4-methoxyphenylthiocarbamoyl)methyl-
[(Ethoxycarbonyl(4-methoxyphenylcarbamoyl)-
methylene]triphenylphosphorane 3e as colorless
prisms (63%), mp 185–187◦C (found: C, 72.5; H,
5.7; N, 2.8. C30H28NO4P requires C, 72.4; H, 5.7; N,
2.8%); νmax (cm−1) 3420, 1732, 1632, 1584, 1288,
1123, 1073, 962, 744, and 723; δH 10.80 (1H, br s),
7.75–7.6 (6H, m), 7.55–7.3 (11H, m), 6.73 (2H, half
AB pattern, J 9), 3.70 (3H, s), 3.68 (2H, q, J 7), and
0.53 (3H, t, J 7); δC see Table II; δP +18.8; m/z 497
(M+, 7%), 375 (96), 343 (35), 303 (25), and 91 (100).
[(Ethoxycarbonyl)(phenylthiocarbamoyl)methyle-
ne]triphenylphosphorane 4a as colorless crystals
(95%), mp 145–147◦C (lit. [4], 147◦C) (found: C,
71.9; H, 5.4; N, 3.1; S, 6.2. C29H26NO2PS requires
C, 72.0; H, 5.4; N, 2.9; S, 6.6%); νmax (cm−1) (KBr)
3450, 1633, 1587, 1547, 1437, 1367, 1313, 1282,
1104, 1029, 748, and 689; δH 12.38 (1H, br s),
7.85–7.75 (6H, m), 7.66 (2H, d, J 5), 7.58–7.50 (9H,
m), 7.28 (2H, t, J 5), 7.07 (1H, t, J 5), 3.56 (2H, q, J
7), and 0.45 (3H, t, J 7); δC see Table II; δP +10.5;
m/z 483 (M+, 8%), 450 (12), 374 (9), 328 (12), 201
(18), 183 (60), 135 (95), and 77 (100).
ene]triphenylphosphorane 2e as yellow crystals
(45%), mp 149–151◦C (found: C, 72.3; H, 5.3; N, 2.6.
C29H26NO2PS requires C, 72.0; H, 5.4; N, 2.9%);
νmax (cm−1) 3440, 1734, 1590, 1542, 1509, 1320,
1106, 750, 719, and 694; δH 7.9–7.7 (6H, m), 7.7–7.4
(11H, m), 6.80 (2H, half AB pattern, J 9), 3.76 (3H,
s), and 1.46 (3H, s); δC see Table I; δP +8.5; m/z
(M+ 483 not apparent), 318 (M+–ArNCS, 20%), 317
(M+–ArNHCS, 19), 303 (85), 294 (35), 183 (35), 165
(100), 150 (60), and 122 (38).
[(Ethoxycarbonyl)(phenylcarbamoyl)methylene]tri-
phenylphosphorane 3a as colorless needles (93%), mp
192–194◦C (lit. [3], 189–190◦C) (found: C, 74.4; H,
5.7; N, 3.3. C29H26NO3P requires C, 74.5; H, 5.6; N,
3.0%); νmax (cm−1) (KBr) 3447, 3250, 1637, 1611,
1586, 1525, 1439, 1301, 1225, 1107, 755, and 693;
δH (CD3SOCD3) 10.99 (1H, br s), 7.75–7.65 (6H, m),
7.65–7.50 (9H, m), 7.40 (2H, d), 7.18 (2H, t), 6.89
(1H, t), 3.60 (2H, q, J 7), and 0.44 (3H, t, J 7); δC see
Table II; δP +18.9; m/z 467 (M+, 15%), 375 (100),
303 (10), and 183 (4).
[(Ethoxycarbonyl)(4-nitrophenylcarbamoyl)meth-
ylene]triphenylphosphorane 3b as yellow crystals
(54%), mp 190◦C (found: C, 68.1; H, 4.7; N, 5.5.
C29H25N2O5P requires C, 68.0; H, 4.7; N, 5.5%); νmax
(cm−1) 3432, 1732, 1597, 1270, 1125, 1074, 855,
742, and 690; δH 11.60 (1H, br s), 8.08 and 7.64 (4H,
AB pattern, J 9), 7.80–7.65 (6H, m), 7.60–7.45 (9H,
m), 3.74 (2H, q, J 7), and 0.56 (3H, t, J 7); δC see
Table II; δP +19.2; m/z 512 (M+, 5%), 375 (100),
347 (20), 303 (36), 277 (96), 201 (25), and 183 (46).
[(4-Chlorophenylcarbamoyl)(ethoxycarbonyl)meth-
ylene]triphenylphosphorane 3c as colorless crystals
(90%), mp 181–182◦C (found: C, 69.4; H, 5.05;
N, 2.8. C29H25ClNO3P requires C, 69.4; H, 5.0; N,
2.8%); νmax (cm−1) (KBr) 3435, 1640, 1615, 1579,
1518, 1306, 1104, and 692; δH (CD3SOCD3) 11.07
(1H, br s), 7.7–7.6 (6H, m), 7.6–7.45 (9H, m), 7.45
and 7.21 (4H, AB pattern, J 9), 3.60 (2H, q, J 7), and
0.43 (3H, t, J 7); δC see Table II; δP +19.0; m/z 503
(37Cl-M+, 0.6%), 501 (35Cl-M+, 2), 375 (100), 347
(10), 303 (30), 301 (45), 277 (35), and 183 (40).
[(Ethoxycarbonyl)(4-methylphenylcarbamoyl)-
methylene]triphenylphosphorane 3d as colorless
crystals (27%), mp 177–179◦C (found: C, 74.8; H,
5.95; N, 2.9. C30H28NO3P requires C, 74.8; H, 5.9;
N, 2.9%); νmax (cm−1) 3430, 1732, 1645, 1620, 1583,
1525, 1290, 1104, 1073, and 721; δH 10.85 (1H, br s),
7.8–7.65 (6H, m), 7.55–7.4 (9H, m), 7.40 and 6.96
(4H, AB pattern, J 9), 3.70 (2H, q, J 7), 2.24 (3H, s),
and 0.54 (3H, t, J 7); δC see Table II; δP +18.8; m/z
481 (M+, 8%), 375 (100), 303 (20), 183 (15), and 58
(21).
[(Ethoxycarbonyl)(4-nitrophenylthiocarbamoyl)-
methylene]triphenylphosphorane 4b as yellow prisms
(41%), mp 204–205◦C (found: C, 66.1; H, 4.8; N, 5.3.
C29H25N2O4PS requires C, 65.9; H, 4.8; N, 5.3%);
νmax (cm−1) 3440, 1734, 1654, 1595, 1557, 1501,
1272, 1109, 1029, 856, 749, and 650; δH 12.90 (1H,
br s), 8.14 and 8.06 (4H, AB pattern, J 9), 7.9–7.7
(6H, m), 7.6–7.4 (9H, m), 3.68 (2H, q, J 7), and 0.60
(3H, t, J 7); δC see Table II; δP +11.8; m/z 528 (M+,
5%), 495 (14), 429 (4), 347 (15), 303 (25), 294 (30),
275 (28), 262 (24), 183 (45), and 43 (100).
[(4-Chlorophenylthiocarbamoyl)(ethoxycarbonyl)-
methylene]triphenylphosphorane 4c as colorless
crystals (92%), mp 173–175◦C (found: C, 67.35; H,
4.9; N, 2.9; S, 5.8. C29H25ClNO2PS requires C, 67.2;
H, 4.9; N, 2.7; S, 6.2%); νmax (cm−1) (KBr) 3436,
1644, 1583, 1546, 1490, 1439, 1312, 1288, 1105,
1026, 831, and 690; δH (CD3SOCD3) 12.34 (1H, br
s), 7.8–7.7 (6H, m), 7.67 and 7.32 (4H, AB pattern, J
9), 7.6–7.5 (9H, m), 3.55 (2H, q, J 7), and 0.44 (3H,
t, J 7); δC see Table II; δP +11.0; m/z 519 (37Cl-M+,
20%), 517 (35Cl-M+, 60), 484 (20), 408 (10), 301
(70), 277 (50), 262 (40), 183 (85), and 169 (100).
[(Ethoxycarbonyl)(4-ethylphenylthiocarbamoyl)-
methylene]triphenylphosphorane 4d as colorless
crystals (56%), mp 169–171◦C (found: C, 72.6; H,
5.7; N, 2.8. C30H28NO2PS requires C, 72.4; H, 5.7;
N, 2.8%); νmax (cm−1) 3430, 1732, 1640, 1582, 1551,
1278, 1100, 1025, 821, 742, and 689; δH 12.22 (1H, br
s), 7.85–7.70 (6H, m), 7.54 and 7.05 (4H, AB pattern,
J 9), 7.50–7.35 (9H, m), 3.64 (2H, q, J 7), 2.28 (3H,
s), and 0.54 (3H, t, J 7); δC see Table II; δP +10.4;
International Journal of Chemical Kinetics DOI 10.1002/kin