320
IVANOVA et al.
3
3JНН 4.7 Hz), 8.46 d (2H, Н2,6, Py, JНН 5.2 Hz). 13С
H 5.81; N 10.85; Р 7.91; S 8.29. С20H22 N3OPS. Cal-
NMR spectrum, δC, ppm: 28.00 (PhСН2), 28.11 d
culated, %: C 62.65; H 5.78; N 10.96; P 8.08; S 8.36.
1
(CH2P, JPC 45.9 Hz), 28.12 (PhСН2), 29.64 d (CH2P,
[Bis(2-pyridin-2-ylethyl)phosphoroselenoyl]-
(pyridin-4-yl)methanol (XXIII). Yield 0.421 g
(98%), white powder, mp 69–70°C. IR (KBr, cm–1):
1
1JPC 46.1 Hz), 72.36 d (PCH, JPC 56.1 Hz), 122.35
(C3,5, Py), 126.45 (Cp), 128.05, 128.19 (Co), 128.57
3
3
(Cm), 140.36 d (Ci, JPC 5.0 Hz), 140.50 d (Ci, JPC
1
1098 δ(COH), 484 ν(P=Sе). Н NMR spectrum, δH,
5.0 Hz), 147.64 (C2,6, Py), 147.93 (C4, Py). P NMR
31
ppm: 2.07 m, 2.45 m, 2.67 m, 2.85 m, 2.94 m, 3.17 m,
spectrum, δP, ppm: 58.5. Found, %: C 69.35; H 6.40; N
3.72; P 8.07; S 8.44. С22H24NOPS. Calculated, %: C
69.33; H 6.34; N 3.67; P 8.12; S 8.41.
3.60 m (8H, PyСН2СН2Р), 5.04 s (1H, РСН), 7.04 d
3
(1H, Н3, 2-Py, JНН 7.4 Hz), 7.11 d.d (1H, Н5, 2-Py,
3JНН 7.2 Hz, 3JНН 5.3 Hz), 7.23 d.d (1H, Н5, 2-Py, 3JНН
3
3
[Bis(2-phenylethyl)phosphoroselenoyl](pyridin-
4-yl)methanol (XXI). Yield 0.407 g (95%), white
powder, mp 146–148°C. IR (KBr, cm–1): 1098
7.6 Hz, JНН 5.6 Hz), 7.32 d (1H, Н3, 2-Py, JНН
7.9 Hz), 7.56 d.d (1H, Н4, 2-Py, JНН 8.3 Hz, JНН
3
3
7.8 Hz), 7.66 d (2Н, Н3,5, 4-Py, JНН 4.2 Hz), 7.72 d.d
3
1
3
3
δ(COH), 479 ν(P=Se). Н NMR spectrum, δH, ppm:
(1H, Н4, 2-Py, JНН 8.3 Hz, JНН 7.8 Hz), 8.46 d (1H,
3
3
2.06 m, 2.21 m, 2.38 m, 2.74 m, 2.88 m, 2.93 m (8H,
PhСН2СН2Р), 5.04 d (1H, РСН, 2JPН 4.2 Hz), 6.59 br.s
(1H, OH), 7.06–7.22 m (10Н, Ph), 7.49 br.s (2H, Н3,5,
Py), 8.36 br.s (2H, Н2,6, Py). 13С NMR spectrum, δC,
H6, 2-Py, JНН 4.6 Hz), 8.50 d (1H, H6, 2-Py, JНН
4.6 Hz), 8.59 d (2Н, Н2,6, 4-Py, 3JНН 6.0 Hz). 13С NMR
1
spectrum, δC, ppm: 24.22 d (CH2P, JPC 40.7 Hz),
1
25.08 d (CH2P, JPC 42.5 Hz), 28.84, 30.11 (PyСН2),
1
1
ppm: 27.64 d (CH2P, JPC 37.0 Hz ), 28.96 (PhСН2 ),
72.45 d (PCH, JPC 43.7 Hz), 121.33, 123.12 (C5, 2-
1
1
29.09 d (CH2P, JPC 38.8 Hz), 71.65 d (PCH, JPC
Py), 121.95 (C3, 2-Py), 122.25, 124.22 (C3,5, 4-Py),
136.69, 137.78 (C4, 2-Py), 144.91 (C4, 4-Py), 147.62,
149.32 (C2,6, 4-Py), 149.26 (C6, 2-Py), 159.61 (C2, 2-
48.0 Hz), 122.31 (C3,5, Py), 126.40 (Cp), 127.85,
3
128.00 (Co), 128.75, 128.78 (Cm), 140.18 d (Ci, JPC
5.7 Hz), 140.04 d (Ci, JPC 5.7 Hz), 147.10 (C4, Py),
Py), 160.05 d (C2, 2-Py, JPC 13.5 Hz). 31P NMR
3
3
147.84 (C2,6, Py). 31P NMR spectrum, δP, ppm: 53.7.
Found, %: C 61.49; H 5.67; N 3.24; P 7.15; Se 18.19.
С22H24NOPSe. Calculated, %: 61.68; H 5.65; N 3.27; P
7.23; Se 18.43.
spectrum, δP, ppm: 54.3. 15N NMR spectrum, δN, ppm:
–72.6, –89.9 (2-Py); –74.2 (4-Py). 77Se NMR
spectrum, δSe, ppm: -413.7 (1JP,Se 707.6 Hz). Found, %:
C 55.69; H 5.13; N 9.69; P 6.99; Sе 18.26. С20H22 ·
N3OPSе. Calculated, %: C 55.82; H 5.15; N 9.76; P
7.20; Sе 18.35.
[Bis(2-pyridin-2-ylethyl)phosphorothioyl]-
(pyridin-4-yl)methanol (XXII). Yield 0.364 g (95%),
white powder, mp 86–87°C. IR (KBr, cm–1): 1083
[Bis(2-pyridin-4-ylethyl)phosphoryl](pyridin-2-
yl)methanol (XXIV). Yield 0.340 g (81%), yellow oil.
1
δ(COH), 614 sh 622 ν(P=S). Н NMR spectrum, δH,
1
ppm: 2.02 m, 2.13 m, 2.39 m, 2.73 m, 2.89 m, 3.24 m,
IR (thin layer, cm–1): 1097 δ(COH), 1142 ν(P=О). Н
3.52 m, 3.65 m (8H, PyСН2СН2Р), 4.94 d (1H, РСН,
NMR spectrum, δH, ppm: 1.85 m, 2.16–2.22 m, 2.38
m, 2.64 m, 3.10 m (8H, PyСН2СН2Р), 5.18 d (1H,
РСН, JPН 8.0 Hz), 5.82 br.s (1H, OH), 6.92 d (2Н,
3
2JPН 2.5 Hz), 7.01 d (1H, Н3, 2-Py, JНН 7.0 Hz), 7.08
3
3
2
d.d (1H, Н5, 2-Py, JНН 7.6 Hz, JНН 6.7 Hz), 7.22 d.d
(1H, Н5, 2-Py, JНН 7.6 Hz, JНН 6.3 Hz), 7.29 d (1H,
Н2,6, 4-Py, JНН 5.6 Hz), 7.19 d (2Н, Н2,6, 4-Py, JНН
3
3
3
3
Н3, 2-Py, JНН 8.0 Hz), 7.53 d.d (1H, Н4, 2-Py, JНН
5.6 Hz), 7.35 d.d (1H, Н5, 2-Py, JНН 7.8 Hz, JНН
3
3
3
3
8.0 Hz, JНН 7.6 Hz), 7.60 d (2Н, Н2,6, 4-Py, JНН
5.6 Hz), 7.70 d (1H, Н3, 2-Py, JНН 7.9 Hz), 7.78 d.d
3
3
3
4.0 Hz), 7.69 d.d (1H, Н4, 2-Py, 3JНН 8.0 Hz, 3JНН 7.6 Hz),
(1H, Н4, 2-Py, 3JНН 7.9 Hz, 3JНН 7.6 Hz), 7.79 d.d (1H,
8.45 d (1H, H6, 2-Py, JНН 4.5 Hz), 8.48 d (1H, H6, 2-
Н4, 2-Py, JНН 7.9 Hz, JНН 7.6 Hz), 8.44 d (2Н, Н3,5,
3
3
3
Py, JНН 4.5 Hz), 8.56 d (2Н, Н3,5, 4-Py, JНН 4.2 Hz).
4-Py, JНН 5.6 Hz), 8.53 d (2Н, Н3,5, 4-Py, JНН
3
3
3
3
13С NMR spectrum, δC, ppm: 24.80 d (CH2P, JPC
5.6 Hz), 8.56 d (1H, H6, 2-Py, JНН 4.8 Hz). 13С NMR
1
3
1
1
47.7 Hz), 25.68 d (CH2P, JPC 49.3 Hz), 28.84, 30.11
(PyСН2), 72.76 d (PCH, JPC 52.8 Hz), 121.62, 123.09
spectrum, δC, ppm: 24.64 d (CH2P, JPC 60.9 Hz),
1
1
26.57 d (4-PyСН2, JPC 3.1 Hz), 26.78 d (4-PyСН2,
(C5, 2-Py), 122.14, 124.08 (C3, 2-Py; C3,5, 4-Py),
136.64, 137.66 (C4, 2-Py), 144.85 (C4, 4-Py), 148.21,
149.22 (C6, 2-Py), 149.02 (C2,6, 4-Py), 159.39 d (C2, 2-
Py, 3JРС 5.9 Hz), 159.77 d (C2, 2-Py, 3JРС 13.9 Hz). 31P
NMR spectrum, δP, ppm: 60.4. 15N NMR, δN, ppm:
–72.7, –88.6 (2-Py); –75.2 (4-Py). Found, %: C 62.49;
1JPC 3.3 Hz), 27.26 d (CH2P, JPC 62.2 Hz), 70.27 d
1
(PCH, JPC 76.6 Hz), 122.55 (C3, 2-Py), 123.30 (C3,5,
1
4-Py), 123.57 (C5, 2-Py; C3,5, 4-Py), 137.30 (C4, 2-Py),
148.16 (C6, 2-Py), 149.90 (C2,6, 4-Py), 150.01 (C2,6, 4-
Py), 150.01 (C4, 4-Py), 153.75 (C2, 2-Py). 31P NMR
spectrum, δP, ppm: 49.9. 15N NMR, δN, ppm: –75.6,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 2 2011